For me, I do 1-2 mins each time, no fixed amount, as long as she’s awake and free, I’ll put her in TT position. It can be from 1-6 times per day.
When he cries, lift him up. Don’t let him associate TT to something detestful, just try again later. If my LO face down, I will just adjust her entire position (arms slightly crossed) then try again. If you adjust his head to face side ways, he’s just gonna lie down there.