Yes it is possible. There are two different cases. One is that you are coming as a tourist. In that case you will have to get Mexican auto insurance before you come. This is available at most border cities but do not expect it to be finished in 10 minutes. Your US or Canadian insurance will most likely not cover anything that happens in Mexico. Ask the insurance agent to explain to you the difference in cost for insurance with representation. You will probably be asked to put up a deposit at the border and they will put a sticker on the car describing its immigration status. This is to ensure that the car leaves when you do. You will probably not be allowed to fly home and leave the car in Mexico.
1..it has to be in his name...unless you change the title...have a notary change the title into your name. Have a registration in your name....that is ok...or a title in your name.
He can get the permisso when he gets here to MX....it doesnt take that long...the office is open 24/7
#2....well if you never come back to the border...you'r ok....but if you want to bring it back up here to the frontera...you will need to have the permisso. They have federal check points somedays...somedays....and the feds are checking for the permisso...they can hassel you over this.
#3 only if you want to...i didnt....i canceled the insurance too...called the dmv...told them i was taking my car to mexico and needed to keep the tag...it's ok.
#3-A....if you make it mexican...you can bring it back and forth.
#4...dont have a clue...you need to so some research...call companies...find out the deal...let us know what you find out...honestly it will cost you more to send it and pay taxes than what the trucks worth...per my hubby...i asked him all these questions...lol
Honestly the cheapest way right now is get the permisso and let time answer your other questions.