If you want a good deal never buy from a dealer. They usually charge full retail, you have no history and service records, and they add in their hidden fees. Buy from a private seller and save yourself some $$.
I would look very hard at auto trader, ebay, craigslist, etc and be willing to drive for a good deal.
Research cherokees on here and do lots of reading about problem points for them before you buy one.
The family friend one for $5800 may be an ok deal depending on condition, but I would expect to get it for 5k. Nice lower mileage ones are getting harder, but you can still find decent ones out there pretty cheap, like $3500 and under.
2001 amber fire cherokee sport 4x4, 2 in lift, 30x9.50 generals, 174 ion wheels, pretty much stock.