I've got a few thoughts as I was in the same predicament awhile ago.
Think about getting under a ten foot beam. You can usually find someone that'll let you loan/rent a trailer. U-haul truck for a few hours and you've hauled your own boat and brought it to your own house/friend's to do bottom maintenance and repair. Or trailer inland to avoid hurricanes while staying at an RV park, I met someone who did it.
Look at boats with a blown inboard. When I was looking, these boats were consistently 4-5 thousand cheaper. An outboard will run you under a grand and are easier to pull off and do overhauls and maintenance. And after you take out the old gas tank (replaced with portables) you'd be amazed at how much space is under the cockpit.
Irwin 10/4s and 28s are found for good deals. I bought my 28 for $4000, sails are a year old and 9.9 Nissan LS is a year old. I basically got the rest of the boat for free. 3' draft, 9'beam, 6'2" headroom, and has a head.
Irwins had issues with hull to deck leaking, but is a fairly easy to fix to re-bed it, as you said you're handy.
http://www.sailboatlistings.com/view/8796http://www.sailboatlistings.com/view/7067http://newhaven.en.craigslist.org/boa/1305168106.html