Re: The Good The Bad & The Ugly
Without more information about what you want to do with a boat it is hard to provide much useful feedback. Boats/motors are often pretty specialized to the usage and environment. For example around here, folks who fish on the rivers tend to run "jets" (outboards that pump water thru a nozzle to provide thrust rather than using a prop). But for wakeboarding they would suck.
As someone who is still on the first boat (but 2nd motor) my advice would be to treat a boat, particularly a used one, as a whole in the water into which you pour money and to which a potentially very expensive and troublesome device called an outboard is attached.
Or put another way, the same hull can be worth $1000 to $10000, depending on what is hung on the transom. Various models and makes of outboards will have their advocates and detractors (except maybe Force, which I have yet to meet and advocate for). As a newbie, the only really safe route is a new, or almost new and still in warranty motor. Safe as in at least the warranty should cover repairs, as long as they are not a result of your errors. This is also the really expensive route, since new outboards go from around $1k (for a small trolling motor) to $20K+ (for the largest).
One advantage of an outboard for a newbie in a northern climate is that winterization is a pretty simple issue. My knucklehead neighbor killed the I/O motor on a brand new Bayliner by not winterizing it properly the first year. It became the 2nd dead boat in his yard, next to the older Bayliner with the rotted out interior, mushy floor, and dead Force outboard.
OTOH, if you've got time and are mechanically inclined, then now might be the time to buy a boat with an older 2 stroke outboard, with the assumption that you'll tear into it over the winter and get it in top shape for next season.
YMMV,
-dm