Hey soundguy you might run over to iboats.com. They have a great forum over there. I can't believe the negative replies about boats. I am 36 and have had a boat since I was 19. The first one I got was a 16' runabout. I did not know anything at all about boats (just been out with buddies a few times) and I ran that boat for 6 years with out any problems at all, I then sold it to little bro and it is still running strong. Our second boat we picked up for 13.5k it was a 19' glastron ski boat, had if for 7 years and sold it for 11.5k. I did not do anything to this boat except add trailer brakes. Our current boat is a 23' deck boat, this one has taken some tlc, but I knew that going in. I think I could actually make money on it right now (had if for 2 years)
I do not think you would have any problems with buying a good used boat. The most common thing you have to do with them is change your impellers (it is recommended once a year, pretty easy), if you use it in salt water you will need to flush it out after every use, but a lot of the salt guys drop in a river and go to the salt, this helps get the salt out of the motor and is easier on the trailer. I know you can handle a wrench, so do not let things scare you off.
The best advice I have read so far, is to rent one and see if it is to your liking. I agree completely.
Good luck, Dave