Penile stimulation would just drown out any feeling in the prostate so I would just orgasm from that and not reach the more "calm" prostate orgasm

Yes. Left to right, not in and out. Since the toy is curved it stimulates the prostate without stimulating the anus which I find makes it easier to feel when I'm stimulating the prostate.

I don't get numb, but it does take something like 20minutes. I have to go slowly and be super relaxed, almost meditating. It's not at all like when wanking.

For me the important thing to reach prostate orgasm is zero penile stimulation, relaxing a lot in a comfortable position, and rotating the toy, not going back-and forth to stimulate the prostate and nothing else.

It's generally easier in something like a bathtub where I can rest my legs high and not have to hold them myself.

Dude here, I don't have much experience without condoms but you do feel much more warmth without.

Still, I'd rather use one and be relaxed about risks of kids/STDs