HELP! Where to start?
I agree with Hamian. Boseyachts must be a broker.
A misconception is that bigger boats are harder to handle when in fact they are safer due to less and slower motion. 28 foot boat are near the minimum or below the minimum if you can''t stand up in it.
Never ever buy a new boat!! Maybe Jeff H could order a new boat because he knows just what he wants but not you.
Buy a Catalina or a Hunter but don''t feel that it has to be almost new. Our boat is a 1973 35'' and there is no way I would trade it for a minute for a new 28'' boat no matter what the money is.
Roller furling/reefing is wonderful. Jeff H puts it down because with a crew he can order sail changes. All of the long distance racers use it. All crusers use it. Most masthead sloops in fact will sail quite well on just the genny.
I had tiller sailboats for 25 years and I am sick of them. I have a wheel now with a autopilot and we love it. But with a autopilot tillers are ok.
I had outboard boats and inboards are better saftey wise as they will not cavitate. I don''t know where Jeff gets the notion that you need to be a mechanic with a outboard. More to the opposite. You can take it off and get it fixed anywhere. A friend has a 26'' sailboat on a 2x20 mile lake and there the 10 HP OB he has is just fine. On the great lakes an inboard is good death insurance.
In summary: Buy a C&C 30 or a Tartan 30 for $10,000. These will be 1970''s boats. These boats will sail well and when you sell it you may even make money if you keep it up.