My buddy Ed contacted me about a finding him a sub $5k car that fit the following criteria:
2:48 PM edwardwilson749: Up for a car challenge?
me: sure!
2:50 PM edwardwilson749: You can take your time with this one, but we are looking for a dog/visitor car. Open to all makes/models with a max of $5000. Looking for something we can haul the 3 dogs in comfortably, let visitors drive when they are here, and not be embarrassed to park out front.
2:51 PM So far we have been looking at wagons, but would be open to a small SUV, or anything if the right one comes along.
me: hmmm, interesting.
2:52 PM edwardwilson749: Figure pick something up, drive it for a couple years, then sell it for a little less than what we paid for it. Figure it’ll cost us a couple grand to own, as opposed to a complete junker that might cost that much in maintenance.
So it will need to have a fairly good service record as well.
2:53 PM And being located somewhere close to the SE as well 😉
me: gotcha, sounds like fun!
You can fake having 3 dogs in a 4 door once in a while, but it’s sure not ideal. In my mind, that means wagon or SUV.
So I took a swing at some logical choices for Ed and G. I may have to come back to this later in the week with some more ‘creative’ examples though!
The first car to spring to mind was an e34 touring, that Ed also had found. His response was ‘meh’ for this 1993 525i Touring on Craigslist for $4k:
Right behind the BMW e34’s on my list was the W124 Benz Wagons:
1995 Mercedes 300TE Wagon on Craigslist in Orlando
1995 E320 Wagon on Craigslist $4595 in Orlando
And if you’re going to consider BMW’s and Merc’s, well you have to consider the Audi’s with Quattro:
1998 Audi A6 Avant on Craigslist Treasure Coast:
Or this 1998 A6 Avant with only 83k miles in Virginia on Autotrader.com:
I’ve always thought a Landy was a sharp buy for the money. I’d take a look at these as well:
2000 Land Rover Discovery on Craigslist West Palm, $4130, 123k miles:
And this 1997 Land Rover Discovery SE with only 92k miles for $4996:
And it’s hard to ignore a Japanese option:
1997 Infiniti QX4 on Craigslist Birmingham ($4950):
But of all the cars I looked at tonight, the value leader and enthusiast bargain has got to be the Volvo R series wagons from the late 90’s. Check out these two barn burners for under $5k:
1996 Volvo 850R Wagon on Craigslist Atlanta. I really dig the beech interior and the stout black exterior. 
And along the same lines, this newer 1998 Volvo V70R on Craigslist Savannah:
Honorable Mentions:
Fiat 500 Station Wagon on eBay (exceeds price limit by $2k 😀 )
dc