Hey EJP!
I did this many years ago and it is a nightmare. Now I did most of it myself, I would never ever do it again. Dealing with the shipping company here and Aduana (Customs) is awful. Long lines, corruption (paid at least 2 bribes) laziness, everything stolen inside the car (there wasn't much to steal...they left the jack, was nice of them) Unless this is a real special car I would find something here and save yourself the time, money and lots of headaches.
You can check the import tax on this website from the Ministerio de Hacienda.
http://www.hacienda.go.cr/autohacienda/autovalor.aspx
Site is tough to navigate just like the whole process. The import tax which will be huge...it will basically work out to double of the blue book price of the car in the U.S. You will also have to pay other taxes, sales tax, consumo tax...there will be other taxes and fees, plates, Riteve inspection. Will this older Jeep even pass Riteve???? This will be on top of shipping costs.
I had a friend use this guy a couple of years ago with good results.
Mike Rappaport
506–2573–3933
CR Cell:
506-8878-0042
US Direct #
727-231-4344727-231-4344
He can arrange the whole thing. It would be the only viable way to go. If you do use him or someone else get a firm price up front and make sure the price includes having the car delivered to your front door WITH the Tico plates already on the car. Don't do any of that 90 tourist visa crap.
Good luck bro and may God of mercy on your soul.