I'm going to preface this by saying that I've only made money on one car I've sold. I bought a '92 Ford Mustang LX notchback SSP coupe from the $2007 classifieds and sold it for $4750. I believe that there were a few reasons for why this car made money and the others didn't:
-
SSP collector crowd (I had a bunch of the history, officer's name who drove the car, pictures of it in service, etc.)
-
'92 was the last year of the forged piston Fox bodys
-
color (black)
-
notchbacks are the most sought-after Fox Mustang
-
It was very stock looking (only changes were Ponys and a 1.5" cowl hood that you would barely notice)
I knew a lot about the Fox body Mustangs, and at the time I bought the car also owned a '92 GT. As others have said, really knowing the model you're considering inside and out will help you to better assess condition and value. I'm usually on the classifieds in model-specific forums, so that helps to get a handle on true market value.
Here's my list when picking out a car and trying not to take a bath on it:
-
stock (or as close to stock as possible)
-
no rust (rust would be your #1 enemy in a deal like this)
-
very good or excellent body condition
-
very good or excellent paint
-
service records or other evidence of good maintenance (so you don't spend a fortune in time/money getting caught up on deferred maintenance)
In the case of the SSP car, I fixed a few things that made the car much easier to drive (Maximum Motorsports clutch cable, quadrant, and firewall adjuster) and also fixed a leak from the air pump (emissions equipment). I also brought the car back as close to stock as possible (aftermarket shifter replaced with a stock one, removed the front strut tower brace, removed the K-member brace). A solid detail job really helped the car look great in pictures...
I think it's possible, getting a fair deal to start goes a long way to not taking a bath. Having the ability to patiently wait for the right buyer is another key component.