As a mostly North American legacy carrier traveler, I'm used to the fairly loose policies, but will be flying SAN-SFO-SIN-DPS soon. (SAN-SFO is on AS sold by SQ.)

My usual rolly is probably oversized and overweight (like most American things) by SQ's cabin baggage rule, and I usually have a small daypack as well. SAN-SFO I doubt they'll even blink, but is it likely I'll get forced to check my rolly at SFO or SIN? Thanks.