Thinking about selling my 2008 Tacoma, how much should I be looking for?

I hear what you are saying. But, I sell stuff private party quite often - turn and burn - (mostly Craigslist and similar sites) and OBO is good to use. You don't have to really mean it, but you get a bunch more offers and can negotiate to the price you have set. That's just my experience though.

 

I'd say around 22k is fair , I'm in roughly the same region and have an '08 DCSB Off Road 4x4 in near perfect condition - resale is pretty high on them in good condition around here . Job market sucks around this area unless you want to work for nothing .
Good luck , keep us posted and sell it private - dealers will just rip you off .
Sarge