the timing of the tassle and silk is so off for mine that most pollen will just fall off before the silk even came out

I’ve had this happen before too; I assume it’s too prevent self-pollination, but is super frustrating. As far as keeping the pollen from blowing away, I read somewhere that the best time to hand-pollinate is around 10-11am, which has worked well for me (but I don’t live in an especially windy climate).