I would try buying used from a marina, and see if they offer warrantys
for the first season (0r even a 60 day warranty) if the factory
warranty has expired, anything thats going to go wrong will most likly
happen immediatly. In a boat 90% of your concern should go to the
engine For you being a beginer I think you should stick with an
outboard, just because they are more reliable, more maitance free, but
a lot of people don't like seeing the motor and they are more espensive
right now, When buying an outboard first off look at the drive if will
be pretty obvious if it ever hit anything, ask if its ever been rebuit,
but basically outobards will run forever, if it starts and sounds good
its a good bet, with i/o's look at the bellows(rubber tubes from
outdrive to boat) if they are brittle they will need to be reolaced
($500) you might want to crack the lower unit gear lube drain, see how
clean it is or if their are little pieces of metal in it (which would
mean the gear case is on its way out) Check to see if their are any
visable water lines on the motor because if the starter or alternator
were ever under they might not last, but basically take whatever you
buy for a test drive, problems should be obvious, check out some
Godfrey Hurricane deck boats, they are everywhere in Florida so you can
most likly get a good deal on a nice boat that fits both water sports,
fishing , and cruiseing, and you can also get them in outboard and
i/o's, but i definitly think mark is right, eventually your kids will
force you to upgrade to a mastercraft or nautique