There's a lot of good advice in this thread, and I will not bother repeating it.
Your gut instinct is correct. If something is bothering you before the purchase, imagine what it would be like just after the purchase...
There are a LOT of used boats available right now; some good, some less so, and some are a lot of crap. If you are honest with yourself about how you will use the boat, you should be able to save yourself a lot of time and trouble by buying an appropriate boat closer to your home waters (New England) than Lake Ontario.
[EDIT] I just wanted to add something that I learned in my own boat search; do not get too hung up on any one deal. If something does not seem right to you walk (or in some cases run) away. There will always be another boat.
There is a member of this forum with an O'day 35 that may fit your need; http://www.sailnet.com/forums/boat-b...432-000-a.html
DISCLAIMER: I own an O'day 35, but have no other interest in the sale of this particular boat.