I've got a specialized mini-pump that has a hollow handle that can carry a patch kit and glue. It has been quite handy.
#6 - So far I've had very bad luck with glueless patches. Perhaps needs better "cleaning". Brand specific?
#7 - Tires are a very dynamic process. While a tube is designed to stretch and an unused patch may not be. If I was going to try it, perhaps lay the patch along the rim. And if small enough, under the rim tape if not affecting tire mounting. MTB tires?
I suppose it all comes down to not trusting the glueless patch from giving me a 20 mile walk home.