Re: 1992 Sea Ray 270 Weekender - OK first boat ?
$15k for a 27' Sea Ray with only 370 hours on it and a trailer seems like a reasonable price. Prices are somewhat subject to geographic location. I bought my 1991 Sea Ray 260ov and a new aluminum trailer for $16k with 700 hours on her.
Also, 370 hours ain't spit, provided everything is mechanically sound you've got hundreds and hundreds of hours ahead with good maintenance.
A 27' boat is pretty big, especially for a first boat. If you've been a captain before and are familiar with how boats handle and what needs to be done onboard you'll probably be fine. However if this is your first ownership experience I recommend starting smaller. Aside from the obvious challenge of maneuvering a larger boat and a new crew you'll also have to worry more about depth, access, and service of amenities like gray water pump out, fresh water pumps, shore power converter, water heater, etc. Just food for thought.
Enjoy your purchase regardless!