Go for it. I'm on the same path, six weeks ahead of you, i just bought it yesterday. I'd recommend boatus for insurance. I can't recommend the credit union i used for my loan.
30 feet is good, can get you 6'4" headroom, a head, shower. 27 is tight but doable depending on the storage space of the boat. I'm seeing decent 30' 's going for $9000.
I'll agree with previous poster that The Complete Sailor is a good book to start with. One maneuver I'd suggest practicing early on is the man overboard drill.
A sailing course may be a good idea. They showed me neat stuff I'd never have tried myself like docking under sail. Some can help you get ASA certified which makes it easier to charter a boat.
As for singlehanding a 30 with little prior experience, I can't see it. You'll need friends to run up the sails while you hold the wheel/tiller, and to (attempt to) push you away from pilings when you're docking. If you want to go it alone once you get the hang of things, look for boats with roller furlers, auto pilots and halyards run back to the cockpit. These things help you keep the boat pointed into the wind while you're messing with the sails.
Last edited by nailbunnySPU; 05-04-2009 at 12:45 PM.