Worrying about and preparing for ever more elusive contingencies can be poison in itself. Kafka's short story "The bunker" pictures this state of mind very well.
There's a ceiling to happiness, though, that's predicated on your tolerance of death and suffering around you. You can't punch through it without advanced technology. But I guess people could instead live their lives stoned on their local mushrooms to achieve the same feelings of happiness.
I'd say that meditation is the best version of wireheading currently known to humanity. I admit that due to obvious problems with measuring happiness, this hypothesis is hard to test.
Yes. Would it be a problem though? If everybody is happy with what they have, then progress is unnecessary or even harmful.