For reduced sail area , ease of handling on larger yachts , consider ketch rig .
A fractional rig 40 plus foot yacht will have a monster main ! 
I am 84 years old and been single handing boats for half a century, and I still don't know half of it, but Foolish makes a lot of good points. But they might just not be good points for your project.
You will not be able to keep a family happy as live-aboards on a boat under 38 ft, and better at least 40 ft. Don't be put off by size, the easiest boat I single handed was a 54 foot fero weighing 39 tons and the most demanding a twitchy little 26 footer. Sure the rig on the big boat was big but there are winches to handle that and the ease of working on a stable platform with decent side decks and room to work makde things comparatively easy. You really do need room for all the stuff that a family needs if they are to be still sailing a decade later - food, water, cloths, knitting, scrabble, internet, power and a chance for some private space.
If you are on your own a 33 footer will be OK, but try to put your family on one and you soon will be on your own,
The techniques for handling big cats and monos single handed are different to those needed on smaller boats but none of it is rocket science and with the second hand boat market as depressed as it is at the moment there are plenty of really well found older boats around. And fitting out for single handed sailing need not cost an arm and a leg. I have just finished fitting out a Ranger 33 as a geriatric single hander with top line stuff - Hypalon rib, davits, solar panel with MPPT controller, 12v eutectic frig, electric halyard and sheet winches, best wheel pilot available, Vulcan anchor on an oversize remote controlled winch, new spinnaker and an internal refit. Plenty of change left from $15,000. And there is a good chance of getting a boat with most of that stuff already fitted out.
And of all of the above the absolute must items were a top notch pilot and top-notch ground tackle. And an absolute must for me, centre boom sheeting after seeing a woman pinned to the cockpit coaming and life line by an end of boom sheet after an accidental gybe. No way could she have recovered by herself.
Select to expand quotePhoenixStar said..
I have just finished fitting out a Ranger 33 as a geriatric single hander with top line stuff - Hypalon rib, davits, solar panel with MPPT controller, 12v eutectic frig, electric halyard and sheet winches, best wheel pilot available, Vulcan anchor on an oversize remote controlled winch, new spinnaker and an internal refit. Plenty of change left from $15,000. And there is a good chance of getting a boat with most of that stuff already fitted out.
I'm just over halfway fitting out a Adams 42 I thought was a bargain not much change from $25,000 now well non actually!
I only dream of the prices for electric winches for a 42 footer but my previous delivery on a Adams 42 with electric winches convinced me I'm going to need these item as I grow older.
Bigger is not better for solo, I'm not sure how well families go in smaller but I have learnt is you can never have enough room!
I really hope I'm still sailing at 85!
I read once that the first four boats you buy are preparation for buying the fifth. I've had a Holland 30, Manitou 32, Tophat, Albin Vega (27ft), and a year ago bought an Adams 31 CC. Bottoman line here is that Shamus shouldn't expect that the first boat he buys will be the boat he actually wants, no matter how hard he plans ahead...
I am sure, you heard of Sir Francis Chichester?
If he could have single handed the yachts he sailed around the globe, especially GM lV., after half of his cancerous lung removed, and GM V. just a year or so before he died at 74, this modern yachts of today with ample navigation and communication, safety and sailing equipment on board could be single handed by a much younger fitter person with common sense and reasonable knowledge of the sea if not across oceans but for a short while.
Select to expand quotePhoenixStar said..
I am 84 years old and been single handing boats for half a century, and I still don't know half of it, but Foolish makes a lot of good points. But they might just not be good points for your project.
You will not be able to keep a family happy as live-aboards on a boat under 38 ft, and better at least 40 ft. Don't be put off by size, the easiest boat I single handed was a 54 foot fero weighing 39 tons and the most demanding a twitchy little 26 footer. Sure the rig on the big boat was big but there are winches to handle that and the ease of working on a stable platform with decent side decks and room to work makde things comparatively easy. You really do need room for all the stuff that a family needs if they are to be still sailing a decade later - food, water, cloths, knitting, scrabble, internet, power and a chance for some private space.
If you are on your own a 33 footer will be OK, but try to put your family on one and you soon will be on your own,
The techniques for handling big cats and monos single handed are different to those needed on smaller boats but none of it is rocket science and with the second hand boat market as depressed as it is at the moment there are plenty of really well found older boats around. And fitting out for single handed sailing need not cost an arm and a leg. I have just finished fitting out a Ranger 33 as a geriatric single hander with top line stuff - Hypalon rib, davits, solar panel with MPPT controller, 12v eutectic frig, electric halyard and sheet winches, best wheel pilot available, Vulcan anchor on an oversize remote controlled winch, new spinnaker and an internal refit. Plenty of change left from $15,000. And there is a good chance of getting a boat with most of that stuff already fitted out.
And of all of the above the absolute must items were a top notch pilot and top-notch ground tackle. And an absolute must for me, centre boom sheeting after seeing a woman pinned to the cockpit coaming and life line by an end of boom sheet after an accidental gybe. No way could she have recovered by herself.
Wow ! Under 15k for all that gear how much were the electric winches ?
I paid 2.5 K for 2 manual self Taylor's !
These guys do some pretty good sailing/cruising vids ( Much better than the Bill and Teds Excellent sailing adventure crap) and they have just posted this one. A tour of a Hans Christian 33. For a 33' boat its pretty good,,, sort of makes me want to gut my boat and do it again or sell it.
A lot to do with weather a boat is suitable for short handed or solo sailing is to do with the setup more so than the size. You mentioned that your dad built a Roberts 43 they are not as fast as some but they are bullet proof I think you could do a lot worse than having a look at one of them. There is no way you are going to have enough room for a wife and 3 kids on a 30-33 ft boat.
Hans Christian 33 T was and is on my ( if I won Tattslotto list ) it wont happen Cant afford ticket 
Select to expand quotetwodogs1969 said...
A lot to do with weather a boat is suitable for short handed or solo sailing is to do with the setup more so than the size. You mentioned that your dad built a Roberts 43 they are not as fast as some but they are bullet proof I think you could do a lot worse than having a look at one of them. There is no way you are going to have enough room for a wife and 3 kids on a 30-33 ft boat.
That's what I was thinking dogs... there's been a few around. I quoted a steel 40 odd in one of my other posts. She looks bullet proof too... zizewi I think it's name was. Not set up for getting out single handed though. Did you see it up at the first posts?
Yeah I did personally I prefer glass. Another option for you would be to look at a boat close to you lots of yanks sail out to the islands decide to go no further and sell the boat so some cheap buys to be had there.
www.boatsalestas.com.au/sail-monohulls/hanse-370e-jem/178662/
www.boatsalestas.com.au/sail-monohulls/catalina-387-dragonfly/162846/
www.boatsales.com.au/boats-for-sale/private/used/SSE-AD-1165106/1989-ADAMS-40?cr=0&psq=%28LengthInFeet%3Drange%5B34..40%5D%26%28%28%28%28State%3D%5BTasmania%5D%26%28%28%28SiloType%3D%5BDealer%20used%20boats%5D%7CSiloType%3D%5BDealer%20new%20boats%5D%29%7CSiloType%3D%5BPrivate%20used%20boats%5D%29%7CSiloType%3D%5BDemo%20and%20near%20new%20boats%5D%29%29%26Service%3D%5BBoatsales%5D%29%26HullType%3D%5BMono%5D%29%26Usage%3D%5BCruising%5D%29%29&pso=0&pss=Premium
or a cheap fixer upper
boatbrokers.com.au/boat-details/?de=169827
And of course one of my favorites twist his arm hard Id say 
www.boatpoint.com.au/boats-for-sale/dealer/used/OAG-AD-12111971/1980-HANS-CHRISTIAN-38?cr=0&psq=%28%28Make%3D%5BHANS%20CHRISTIAN%5D%26%28%28%28SiloType%3DDealer%20used%20boats%7CSiloType%3DDealer%20new%20boats%29%7CSiloType%3DPrivate%20used%20boats%29%7CSiloType%3DDemo%20and%20near%20new%20boats%29%29%26Service%3DBoatsales%29&pso=0&pss=Premium
Harken make a small one, plenty of power but they cant hold the tension without winding out. Solved by leading the tail aft to the secondary and using its self tailer as a cleat near the wheel. Out sailing now so not near my invoices at the moment but the cost was remarkably OK. The main sail bits and pieces are handled by a Maxwell Anchormax on the cabin top and that one was less than $700. It does pay to shop around of course.
I set the Maxwell up with a battery isolation switch near the top of the companion way rather than a foot switch and it spins all the tome I am using it so I don't need to stand on a switch, I can just slacken or tighten the tail while I watch the battens dodge the lazy jacks. The electric is faster than by hand so it is easy to time the hoist past the things get in the way. And I love my Lewmar clutches, so easy to let go under load and so easy on the ropes.
Plan B if the electrics fail is to tail across to the manual winch on the other side of the cabin top. Plan B if the sheet electrics fail is to lead aft to the secondary. Plan B on the plotter is a hand held GPS, plan C a hand held prismatic compass. Plan D is to cry a lot.
Select to expand quotetwodogs1969 said...
Yeah I did personally I prefer glass. Another option for you would be to look at a boat close to you lots of yanks sail out to the islands decide to go no further and sell the boat so some cheap buys to be had there.
Why glass preferably?
Select to expand quoteSemusMcgilicoty said..
twodogs1969 said...
Yeah I did personally I prefer glass. Another option for you would be to look at a boat close to you lots of yanks sail out to the islands decide to go no further and sell the boat so some cheap buys to be had there.
Why glass preferably?
Rust 
who said that
depends of who and how good was there assemble and care building and the prep work insulating the steel hull
Ive seen a steel boat grounded and after high tide sail away with a few small dint's . You wont get that in a fiberglass boat.
Its choices
What ever you buy look closely and with that sort of money I would be finding a really good surveyor you can trust for rust if its steel . and also looking very hard my self
Ive shown this before trust no one but your self
I found this hose from the engine sea cock the weekend after a survey
if you are considering a steel boat the book that this mob wrote about building their steel cruising yacht is a good read:
www.yachtmollymawk.com/about/
www.yachtmollymawk.com/books/how-not-to-build-a-boat/
I am really sorry to say, l never ever met a decent surveyor, yet.
The ones l had the misfortune to know were useless as tits on a bull.
They know how to charge, like a wounded bull, but to
o b j e c t i v e l y survey a vessel, no, no way.
I dread to use any of them again.
I think we are talking about another mafia type set up.
The insurer is the real scumbag and the surveyors live on their leftovers like rats. Struth!
just let me know where to see the bill for the above
http://www.gumtree.com.au/s-ad/taperoo/sail-boats/adams-35-yacht/1106696874
worth a look
www.gumtree.com.au/s-ad/outer-harbor/sail-boats/adams-12-cruiser-racer-yacht-aft-cockpit/1080480610
wet dreams are over 
Select to expand quoteSemusMcgilicoty said...twodogs1969 said...
Yeah I did personally I prefer glass. Another option for you would be to look at a boat close to you lots of yanks sail out to the islands decide to go no further and sell the boat so some cheap buys to be had there.
Why glass preferably?
It is a personal thing but for me ease of maintenance. I don't plan on hitting things so steel or aluminum's main plus is can hit rocks and sail off with a dint so don't want to go to the extra maintenance program steel requires. I love the look and romance of timber but again not the maintenance.
Select to expand quotetwodogs1969 said..SemusMcgilicoty said...twodogs1969 said...
Yeah I did personally I prefer glass. Another option for you would be to look at a boat close to you lots of yanks sail out to the islands decide to go no further and sell the boat so some cheap buys to be had there.
Why glass preferably?
It is a personal thing but for me ease of maintenance. I don't plan on hitting things so steel or aluminum's main plus is can hit rocks and sail off with a dint so don't want to go to the extra maintenance program steel requires. I love the look and romance of timber but again not the maintenance.
Spot on. Steel yachts are mainly for those who lack confidence in their sailing and navigation abilities as most steel yacht aficionados say "You can bounce them off rocks with out putting a hole in them." That is like speaking it into existence.
Further, the life of fibreglass has not yet been determined. Construction in fibreglass became mainstream 1960s. I recently sold an S&S34 that was built in 1969 that had experienced a hard life and it was solid as the proverbial brick out house. Relevant article here:- www.ericgreeneassociates.com/images/Boat_Longevity.pdf
I have owned plywood, aluminium, fibreglass and one steel yacht. I would go with aluminium or fibreglass any day, but never again steel.
For yachts 35 to 55 feet in length or more, aluminium is ideal. Weight for weight it is stronger than steel.
For yachts 35 feet and under, fibreglass is an immensely strong material.
I'm with Cisco. Did I tell you guys I did the unthinkable and managed to centrepunch the end of the dock a few weeks ago? It was a hard enough hit to knock the poor foredecky off his feet, and all it did was mark the paint on a pure glass boat.
All comes down to the quality of the construction I suppose.
SB
How was the Easter sail Shaggy?? Inspiring enough for you to enter the race next year???
Hi Cisco,
The 1.5kn true wind at the start wasn't doing much for me! Mind you, we snuck out through Pearl channel and popped out behind Black Jack as we headed up outside of Bribie, before turning back, a nice lazy reach across a long low wave pattern, just spectacular as we met the rest of the fleet coming north. I could have died on the spot happy as a pig in muck
SemusMcgilicoty
members.optusnet.com.au/coastalcruising/introcruising.htm
This would be a good read for you
Select to expand quotePhoenixStar said..
I am 84 years old and been single handing boats for half a century, and I still don't know half of it, but Foolish makes a lot of good points. But they might just not be good points for your project.
You will not be able to keep a family happy as live-aboards on a boat under 38 ft, and better at least 40 ft. Don't be put off by size, the easiest boat I single handed was a 54 foot fero weighing 39 tons and the most demanding a twitchy little 26 footer. Sure the rig on the big boat was big but there are winches to handle that and the ease of working on a stable platform with decent side decks and room to work makde things comparatively easy. You really do need room for all the stuff that a family needs if they are to be still sailing a decade later - food, water, cloths, knitting, scrabble, internet, power and a chance for some private space.
If you are on your own a 33 footer will be OK, but try to put your family on one and you soon will be on your own,
The techniques for handling big cats and monos single handed are different to those needed on smaller boats but none of it is rocket science and with the second hand boat market as depressed as it is at the moment there are plenty of really well found older boats around. And fitting out for single handed sailing need not cost an arm and a leg. I have just finished fitting out a Ranger 33 as a geriatric single hander with top line stuff - Hypalon rib, davits, solar panel with MPPT controller, 12v eutectic frig, electric halyard and sheet winches, best wheel pilot available, Vulcan anchor on an oversize remote controlled winch, new spinnaker and an internal refit. Plenty of change left from $15,000. And there is a good chance of getting a boat with most of that stuff already fitted out.
And of all of the above the absolute must items were a top notch pilot and top-notch ground tackle. And an absolute must for me, centre boom sheeting after seeing a woman pinned to the cockpit coaming and life line by an end of boom sheet after an accidental gybe. No way could she have recovered by herself.
I have one thing to say to you Sir... you are a legend!! I hope I'm still as full of life as you are when I'm 84. 
I am looking at the Sail Chute, it might fill in the downwind dead band where the asymmetrical won't work and it looks like it might be OK single handed. Has anyone had any experiences with these kites?
Couldn't agree more - the only strife I ever got into with second hand boats were the ones I paid to have surveyed. I cant remember a surveyer finding anything I didn't already know about and they all missed expensive problems.
