Yes, I would go to Maho on Sunday. There will be a TON of planes coming in on Sunday, so that's always fun to watch. You can go to Orient any day. Cruise ship crowds really don't affect it there much.

How much are you paying for the jeep, versus a larger SUV, or something like that? There is certainly no reason to rent a jeep because of not being able to navigate roads. And most of them don't have windows, etc. so you won't be able to use a/c to any extent. I seriously like my a/c on island. And if you get caught in a rainstorm, you will probably get wet. Get a regular car. The criminals will know you're a tourist regardless, but make yourself more comfortable, with a larger, regular car.