s o wrote:

1. 1987 Bayliner capri 1950 open bow with 5.0 v8 omc (with 414 hours).
The current owner(2nd owner) has had it for the past 15 years and has
meticulously maintained it and has almost all records from the same
boat shop.

This would be VERY good in my mind. If he had the boat for that long
etc, it must mean the condition was OK after the 5 first years, and
with that maintenance it shouldn't be in such a bad shape...

Still, 20 years is A LOT for a boat engine (especially if it's not
diesel). At least the engine would need a rebuild if it's not done
already? 414 hours means not very regular use, so there might be some
problems anyway due to long periods of non use?

he also redid the floor and stringer 2 years ago (the wood
was treated with fiberglass).

A new floor can hide lots of problems underneath. Is there any way to
tell? Any inspection hatches or can you measure moisture (when the boat
has been out of water)?

If wood is treated with fiberglass it usually means it no longer was in
a perfect shape. But I wouldn't think that would be so serious,
considering the age of the boat?

Maybe he wants to sell the boat because there's problems under the
floor, or maybe he doesn't want to pay for the engine rebuild. Or maybe
it's just getting too old/small/whatever for him...

interior/exterio is in fair condition. boat was used for skiing in
fresh water. comes with galvanized trailer.

If he only used it for skiing, there might not be structural damage in
the hull. I gather Sea Rays are built a bit heavier than Bayliners, so
if a Bayliner is driven regularly in a rough chop, the glassfiber loses
its stiffness.

Does the seller seem a very trustworthy person?

2. 1987 sea ray 17 ft seville open bow with a 1992 120 hp evinrude. i
don't have much details on it yet. will go see it tomor. comes with
gavalized trailer and ad says well maintained.

My experience is that "well maintained" and "good condition" can mean
anything.

the sea ray is about several hurndres $ more, both are under $4000.

"Several hundreds" is peanuts in boats. In addition to the buying price
one needs to consider how much it costs to repair the boats, if that's
even possible.

Well, just my feelings on the issues. Personally I wouldn't probably
dare to buy a boat that's 2 decades old

PS. Regular disclaimers apply...