Well we always talk about cars on the high end, new cars, etc. Lets talk about some affordable but not total ****box used cars.
For me, in the used car arena, one thing I always look for is an older owner who meticulously maintained their car. This sometimes means you are buying a dead person's car, that was the case with my 1991 Cadillac Brougham and my 1995 Cadillac Fleetwood. Just because they are old peoples cars doesn't mean they are stodgy, uncool, etc.
Also I will give you a tip about buying cheap Cadillacs. Stick to the old RWD sleds with a good maintenance history, avoid ANYTHING FWD with the Northstar V8. The newer CTS, STS, XLR, Escalade, SRX, are much more reliable than the 90's/early 00's FWD Northstar cars.
As for products in the Toyota family that are under $8000 used, I highly recommend the 2000-2004 Avalon, if you want a cushy commuter car that is decent on gas, 22 in town, 30 on the highway. What I really like about that gen Avalon is that it has more space than the older LS400, gets better gas mileage, rides just as nice, is just as quiet, has a bigger trunk, ie its really practical for a big sedan.
Our family has a 2000 Avalon with 250k on the clock, original springs, shocks, engine, transmission, paint, interior, etc. That car drives really nice, rides great, interior looks absolutely mint, engine/transmission shift/run like a new car, everything electric on that car works. Exterior wise the paint still looks great until you realize how many rock chips it has and the paint has completely faded off the mirrors, but other than the dings/scratches you see from that many years of use, it still looks like a car you would feel proud to pull up into the valet lane at a fancy restaurant.