I just finished doing the rear main on my Tahoe. I dropped the transfer case and transmission to get at it. I did get a proper low profile transmission jack which was very useful. I'm not sure exactly about your specific questions, but I think pulling the transmission is easier, just get good jack stands that can safely hold your truck high enough for you to work.
The rear main seal I got had an insert that made it possible to install without any special tools. The only mistake I made in doing mine is that the rear main seal has Teflon and the crank side of the seal is not supposed to have any lubricant of any kind applied. I did apply a thin coat of oil. So far no leaks though.