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Lately I been liking the Bayliner Bodega 40' -- early 80's models have nice interior arrangements, aesthetically pleasing* (in other words, not ugly like the big Chris Crafts), and there seem to be enough of them around, they aren't a floating mystery model. They can be found commonly between 40k to 60k, which is a fuckin good deal considering its rivals are double that.
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I grew up on, in, and around boats. I've also worked on them and sold parts for them. I recommend you do a lot of research on Bayliner before you consider investing in one-there is a reason they are cheap....they
are cheap. Admittedly, my experience with Bayliners is mostly with somewhat smaller fishing/pleasure boats(like 25-30'), but they are famous for being underpowered, and have poorly constructed hulls with bad lines. This results in a pig in the water. That might not seem like such a big deal-and on a sunny Saturday it isn't, but if you're gonna live on the thing eventually you are going to get caught out in bad weather-power is one of the things that keeps the dull side down in heavy chop, and keeps you off the fucking rocks!. (I got the feel from the thread that you don't have a lot of boating experience-trust me, first time you have to deal with a gale you will shit yourself, you'll notice when it's over....assuming you're not swimming
)
I like your idea, though, I've thought about it often myself. I'd go the blow-boat route, but it's not a bad idea in any event and you really don't usually get fucked with much. In fact, the CG is probably the easiest LE to deal with there is, at least in terms of hyper-testosterone silliness-they spend most of their time on search and rescue and actively request assistance of us mere "citizens". Granted, this is in the Great Lakes, where "interdiction" isn't such a big deal, and rescue operations are virtually constant(the Great Lakes account for more shipwrecks and loss of life than
http://www.northernmaritimeresearch.com/shipwrecks-causes.html any stretch of Ocean of comparable area, deadly ponds-bad weather, short waves, and big fucking rocks.) so I might be familiar with a whole other CG ...harbor patrol and frickin local cops ARE something of an issue at times. (though I did put a CG petty officer in jail once when I was a bouncer-just a drunk tank kinda thing, got him with a criminal trespass that the owner dropped on the condition of a $200 donation to the Humane Society, and never come back, the way we usually did it with assholes who tried to start fights and refused to leave.)
Have you thought about getting started in something smaller? Get an idea of what you like, don't like, etc? You should be able to get into a seaworthy small-craft for a few grand, play with it for a summer, and sell if for...a few grand.(In fact, I actually have a 1983 24" IMP Inca for sale in that range-twin 140 mercruisers, great ski boat-needs work though) Anyway, there are three basic things a powerboat can have: speed, comfort, and economy. You can have any two.
Chris-Craft is likely the best quality pleasure craft/ cabin cruiser made, IMHO.