We did this about 3 years ago so I have some advice, though my wife is a citizen so our process was different.
The way the containers work is you buy either a half or a full one and put whatever you want into it, including a car. I assumed they would have a platform to install in the container over the car so you can pack things above it - not true. all the space in the container above the car is wasted. Since the car took up half our full container, you'll need a full container unless all your stuff will fit into your car. (BTW, the moving company told us not to put anything in the car. I wish I had packed it full since customs here didn't care, and neither did the shipping company.)
You can only bring a car you've owned (been on the title) for at least 1 year in the US. Also, you can't sell the car here, or allow anyone else to drive it, for 2 years after arrival. Don't think you can sneak past this. We've had inspectors show up at our door wanting to see the car and asking who was driving it.
Parts here for foreign cars are EXPENSIVE (a fuel pump and filter for my Mercedes were US$1000 each) and you're not allowed to bring any with you. If anything needs to be done, fix it before you leave. That means tires too.
Parts are so expensive due to import taxes. You can find domestically fabricated parts for less, but the quality is terrible. Bringing a make that has a factory here would help with maintenance costs. Ford, Chevy, VW, Toyota all have dealerships here but I don't know about factories. Buying something here can mitigate ongoing maintenance costs.
Expect the car to sit in customs about 4 months, and it took ours about 6 weeks to get here from San Francisco. Also expect about $5000 in "unexpected fees", probably depending on the make of the car (we brought a BMW). The customs system, and all government, is very corrupt.
Considering everything, i regret bringing our car. Sticker shock here would have been tough, but the accumulated costs and effort to get it in the country have made it difficult to justify. Though you're right that cars sell for more here than in the US, all the other fees and such add up fast. Check here for local prices: http://listado.mercadolibre.com.ar/camionetas#D[A:camionetas]
I see quite a few older options for about US$10K, and new for US$20K
I didn't answer any of your specific questions, but I hope this helps.