Thanks for the tips. I'm glad I have asked this question before too late. Since I'm riding only a hybrid, I'll just pump it when it needs it. Some day I may get a Topeak Road Morph suggested here.
You're approaching this somewhat backward. Rather than worrying about the tube, practice pumping until you're comfortable knowing you can pump it reliably without breaking the valve. It isn't repeated wiggling, it's more a matter of one time excessive force.
Twice so far this season, I've stopped to help cyclists stranded because they broke the valve pumping the spare after a flat. If you can't pump a repaired tire without braking the valve, the pump, tire levers and spare tube are totally useless and you might as well leave them home.