If it did there wouldn't be a single seed to collect. Even in natural areas of growth flowering would be oddly rare. Perhaps why they dont flower commonly is by the animals who feed off of them.

Over time the portulucae had evolved a different way of propagating that involves being dependent on the very same animal to feed off it and leave behind it's left over. If not for this one animal feeding off of them the portulucae would of long sense be extinct..

Ok to keep my plants outside? Yes you could by your plant heartiness zone 50 F is a safe window. As temps can sometimes drop lower and faster than we would want 50 f is a marker to consider bringing in if in colder temp zones. Iffy: if you want to bring in then bring in if not then keep a eye for low temp changes.

Crassula and kalanchoe bloom ?

All things considered crassulla by type ? and your area climate and micro climate factors would be something to learn. I dont have any buy I'm pretty sure the same area climate/ micro climate would be of some concern for kalanchoe