What is your foolproof method for seating tubeless road tires on 28mm rims?

[RyanAP]

I recently upgraded my road bike to a tubeless-ready wheelset and installed tubeless tires, but I'm having a frustrating time getting them to seat properly and hold air consistently. I'm using a floor pump with a booster chamber, but one tire still has a section of the bead that won't snap into place, and I'm worried about damaging the rim if I use too much force or try an air compressor. For cyclists who have made the switch, what's your foolproof method for initial setup and seating? How much sealant is ideal for a 28mm road tire, and what are the signs that a tire is truly properly seated versus just temporarily holding air? Once set up, how often do you find yourself needing to add air or top up the sealant compared to traditional tubes?