In my opinion any trip 5 days or under is a carry-on. MG is correct in that your needs for the trip described are minimal. A couple of clean T’s some fresh boxers and the rest you can find when your there (so to speak

).
True, you will have to tug that roller board thru the airport, maybe two if you have a connection. That can be a bit of a pain. But, I have never had my carry on bag get lost, or not make a connection, or have to be delivered to a hotel the next day. Imagine if you are there for only a few days and it takes two before your bag shows. What a hassle. And (although it has never happened to me) I wonder if they would even get your bag to Jaco or if you would some how have to get it from SJO??? Too much stress for me on a short trip. Has anyone had this happen? Do they deliver?
If your going for more then a week or have some other compelling reason that requires a check bag, so be it. But with each connection you double the chance of the bag ending up some where other then where you want it. This does not even take into account the added hassle and time of waiting for your bag to make it to the carrousel. That can make a big difference on the return if your connections are tight.
Having done both I can also make a the very vague statement that my bags entering the USA have been far less subject to added searches reentering when I only have a carry on then when having checked. Never once when I had a carry on, out of 50 trips and I would guess 1 in 10 with a checked bag. 2 in 20? Not very scientific and perhaps subject to debate, but that is only my experiences????.
If you want to get booze/liquid or a large amount of gifts back, you could always buy a cheap bag or duffle and pack the stuff up as tight as possible and hope for the best. Heck, that is all your doing with any checked bag.
In the end to me it is a BIG difference and as MG said “keep it simpleâ€
take a carry on!
And either way have a great trip!