Reminds me of an old joke
Q What is the second happiest day in an aircraft owners life ?
A The day he takes possesion of his aircraft
Q What is the happiest day of an aircraft owners life ?
A The day the buyer takes possesion of his aircraft
Seriously though I think it is important to make some long term decisons before you start looking. Why and how are you going to use your aircraft. If the aircraft is a stepping stone to a larger more capable aircraft then the resaleabilty is probably the most important consideration. Airplanes are very easy to buy but very easy to sell. Find a 6 month old issue of pilot and compare the adds to this months issue. I bet you will find many of the same aircraft advertised. On the other hand if you are winding down into retirement and this will be your last aircraft than the long term maintainabilty is more important (ie where are the parts going to be sourced and what will be the maintainance scheme used).
If asked for advice on the subject I have a few general rules
1) Buy the best airplane ( ie good engine, good radios, good, paint interior, good maintainace history) you can find as it will be the cheapest most hassle free choice in the long term
2) Private airplanes don't wear out , they die of neglect from lack of use. An airplane flown regularly will always be a better deal than one with long periods of sitting
3) Keeping an aircraft inside does more than keep the paint shiny, it protects every system in the aircraft from deterioration. An aircraft that has always been hangered will always be better than one which had been left outside for 30 years.
4) The maintaince records don't just detail the work done they give you insight into the mentality of the owner. Evidence of regular work at the same establishment with snags fixed inbetween inspections is evidence of a carefull and conciensous owner. Spotty records from ahost of different shops are the opposite.
5) Stay away from odd ball, low production, orphaned aircraft. They may be cheap to buy, but everything after that will be difficult and expensive.