I suspect you'll get two distinctly different answers here about gearing.
NR, do you want to go first? cause, I'd probably start off with something like this...
"if you want to give yourself a hernia, then definitely consider the 53"
otherwise...
As far as the Royal Farms question: I make some loose guesses on the risk, usually leaving the bike, but keeping it within sight from inside the store. There are a couple of little theft prevention things you can do that will slow down a thief: after stopping move your shifters several clicks out of wack making it likely that a thief will throw the chain, loosen the seat post bolt, or NR's trick- tie a strap around one brake lever.
BTW welcome to the thread nbac23