The only time I require that the pitot static nad transponder check be completed is if the first flight is to be made underneath the mode C veil of a class B airspace.
Is it a good idea to have it done? Yes, especially if there is all fancy glass that requires good pitot static information. And especially if the first flight is made by a low time/inexperienced RV pilot. The reality is that all of our RV's can be safely flown just by looking out the window, but it takes discipline to do that and not pay atention to erroneous airspeed indications and/or alarms.
I watched a 30 year airline pilot at our home community land hot and flip his super cub over because he locked onto an erroneous airspeed indicator that had a pitot leak in the hose at the connection (unbeknownst to him at the time).
I'm sure there are those on this list who have taken off with the pitot cover still attached and the airplane flew quite safely (VFR, of course!). Some of us will admit it, and probably some won't.
Vic