Don't feel too bad -- yours is a somewhat typical story, or at least one we hear here often enough.
I can't really answer your question -- too many different kinds of owners to generalize. But I can offer a little advice.
First, if at all possible, try to confine your search to your local area. This will save you a lot of potential grief and aggravation. Driving a half hour or so to look at a badly neglected boat that has been represented otherwise is a learning experience. Driving 300 miles roundtrip is an exercise in pure frustration.
Also, while I do not know what your price range is, I can say that it rarely makes good financial sense to travel far and wide in search of relatively low-cost sailboats. Time, travel and transport expenses can eat up much of the "bargain" these boats represent. Not to mention the added leverage the seller has when they know you've come all that way.
Finally, try to narrow your search to one or two particular models that would work well for you, rather than whatever boats are being offered in the current classifieds. That way you can become, if not an "expert", then at least confident in your ability to size up individual examples. Be patient, and with your new-found knowledge you will recognize the good one when it eventually turns up.
And, after seeing how poorly some boats are treated by their owners, be prepared to pay a fair price for the one that's been lavished with care and upgrades.