One other thing. The market being what it is and car sales in the toilet you should be looking for "steals" not "average" blue book. If I could get that Subaru for something close to $2300 after inspection, I'd buy it and plan to put $1500 into it. I'd call around until you found a shop in the town 300 miles away that will look it over. DO NOT TELL HIM YOU WILL NOT BE USING HIM IN THE FUTURE. You want him to believe he is working up a job order so he finds _everything_ wrong. Expect to spend a couple hundred bucks. If the mechanic comes back with nothing major ($2000 or so in needed repairs for a handful of things. $300 for new brakes, $400 for new head gasket, $100 for new belts, $150 for an alternator, etc). If it's in the $2000 ballpark, I'd buy it and drive it home. Anything more I walk away.
Assuming you buy, ....First thing I'd do when I got home is take it to my own mechanic and have a full workup done on it. Yes...another couple hundred bucks, but you can't use the mechanic 300 miles away now can you? He should come back with a similar set of stuff that needs to get done (maybe not identical, opinions could be different on what is necessary and what isnt). Use some common sense and pick off the things that seem critical. (no..you don't need your fuel line flushed. Yes you probably need new gaskets or a timing belt) Drop $1000 on whatever it needs. Pay attention to major engine components and brakes first. Now go to the local tire place and drop $500 on new tires (I love my Michelin HydroEdge).
Do regular oil changes and pick off some of the straggling stuff from the "workup" as you get more money, and you should be good for another 100,000.
I would never buy a car from a "friend". Too much can go wrong and make that relationship "weird".
If you pass on both cars...use
http://www.kbb.com to check the price of used cars. Take $1000 off whatever they say due to current market conditions. That would be my max purchase price. May want to even get a carfax report. Only runs a couple bucks and could save you the hassle of driving out there. You'll need the VIN. Tell the guy you are going to run a carfax and see if he stumbles over himself or if he says "everything is clean...here's the VIN".
-Tyler