I brought my baby, my little red sportscar, a Mazda Miata. I have four main problems, but they are not insurmountable:
1) Going through the drive-through of a fast-food restaurant, entering a place that has controlled entry via a gate that you have to press a button to open, or anything involving having an assumption made about your driver's seat being on the right when you roll down your window...all that is awkward, but there are comical moments.
2) Passing a car ahead of you, being able to pull out to the right far enough to look for oncoming traffic, yet tuck back in quickly if a car is coming the other way
3) People at roundabouts tend to assume the passenger in your car is actually driving, so they look at that side of the car for an eye contact. If your passenger is not watching them, they assume they have enough time to pull out in the roundabout, even if it technically isn't their turn, and even if you, the driver, *were* looking at them.
4) Windshield wipers give more clean area to the driver. In the case of traffic driving on the left, the more important area to be looking for oncoming traffic is out the right area of the front windshield. But the top right corner on a left-hand drive gets the least clean...because of the location of the wipers.
As for taking your test in a left-hand drive car...DON'T. Trust me, take driving lessons and use the instructor's car for the test. If anything, you won't have to go out and buy additional insurance for the person giving you your test...it's automatically arranged in a driving instructor's car.
I have not had trouble getting insurance for my car, but I went through Norwich Union and this seems to be one of a very few companies that will insure a US car. Now that my car is 11 years old, it falls into a distinctly unpopular category and Norwich Union was the ONLY insurance company that would take me on, even though I have never ever had any claims/accidents/parking tickets.
As for resale, my particular car may still be worth $7-8 thousand dollars in the US, but it worthless here. I once tried to trade it in and the dealership was going to CHARGE me £500 to haul it away.
Would I bring it if I had it to do all over again? I'm on the fence here. I love having it here, but it's almost like a behemoth now that it's aging. Oh, it still looks and runs great, but sometimes parts are hard to come by. I'd be sorely tempted to get a new car to replace it, but...nothing wrong with it, it's paid for, why bother? So for now, I am running it until it can't breathe anymore.