Buying a used car - seems intimidating.

I'm searching the classificado's, facebook, etc.  Looking for an SUV for around $5k-$7k. I've been looking at some of the 3rd gen 4runners for example.  But people post so little about their cars it's hard to get a sense from the ad.  I know there have been a ton of "buy or ship" posts, I've read a bunch of them.  I'm pretty street smart but have still done the run around many times, travelling an hour to look at cars that are not what they say, bad papers, etc.  And my Spanish is not good enough for that conversation.   

Are people even ok with you taking it to a mechanic?   

Island miles are hard on a car, and there can be invisible water damage.  I have a very nice 4WD 1998 4runner with only 130k miles that looks new.  I could sell for $4k here (due to has some minor hood damage).  But it would last me 10 years on the island. Shipping+tax is $3,500 to get it down there, so my break even is about $7,500 if I sell and then buy something there.  But the paperwork and 10 months to get title don't sound  fun.   I see a few decent ones in that price range, but not sure I want to run around for 2 weeks disappointed and confused and not knowing what I'm buying, whereas I can take the hit on shipping and know I'm getting a dependable vehicle in good condition.  I'll be in Rincon, so that is going to make it that much more challenging not being near San Juan to find a vehicle.

   Is it pretty easy to find a decent SUV for $6k+ that is not a rusty rattle trap and going to leave you stranded? Or is it just easier to bring one down? Thanks.