SoCal ViperClub went to a Meguiars hands on detail seminar.
Presenter asked...how many want a show car quality detail? Nearly every hand went up.
He then explained that in order to get that show car quality, quite a bit of the clear coat needed to be removed, and indicated that typical vehicle has only about 3 of them before the clear coat is gone.
Most detailers have a little gadget that they use to measure the paint/clear coat thickness. They measure in many different places, as the edges typically get worn off first.
Only way to know for sure, on your car, is to get it measured.
Vipers tend to have a very hard and durable clear coat, however everything has it's limits.
Your idea of starting with a random orbital buffer is good. They do not tend to remove as much as a spinning buffer. Save a little paint for down the road : >)