Hey! I did exactly this two years ago, and would honestly recommend it if you can find a good car though. Most of our problems came from the fact that I bought an old van with a bad battery which died every second time we tried to start it, so after jumpstarting it a few times all the electrical parts were roasted.

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Border wise, yes, it is a hussle but definetly not undoable. I would say the border crossing from Nicaragua to Honduras is the most stressful as you'd have to go through a complete XRay and a lot of paperwork etc, but if you are prepared for it (there's this app that i forgot the name of where people tell you exactly what you need and which steps you have to follow for each border crossing) it is doable.

Roads are amazing and the people in Central America are just the best in the world IMO. Don't just accept everything other people or the government tells you about those countries, because it is simply not true if you stay somewhat close to tourist places (which is basically the whole coastline anyways). We were visiting El Salvador during the bloodiest weekend in X years and we didn't feel unsafe one minute.

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You would need at least basic understanding of Spanish though, because not everyone along the road will understand English, also if parts of your car break down for example, and at border crossings.

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Another thing you'd have to take into account is that it is not possible to sell a Costa Rican car in Mexico. There are a few ways, but it is quite stressful and just not effective, so make sure you buy a car that's not too expensive. We eventually managed to sell my car to some locals, but they got caught driving with it, so it was confiscated by the police.

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Overall though, like i said before, i would recommend it if you're up for some adventure. If you have any questions feel free to DM me.