I'll try to answer your questions to the best of my knowledge.
1 - The computer is always learning, it never stops. It probably takes a couple of hundred miles for it to learn after a re-program, but even after it learns the maps, the ecu will always make adjustments as needed. Fuel/air ratios and such are always changing, so it actually never stops learning, but then it's more fine tuning for optimum performance.
2 - r/t maps have to be learned just like the base maps. You could re-flash, but you would want to drive it some, to get the ecu accustom to the new map for best performance.
I hope I didn't confuse you more!