Being a lefty, I also encounter similar issues, so here's my two cents regarding pocket carry:
My Timberline knife switches to the right side front pocket.
My Kel-Tec, or snub, in DeSantis Nemesis holsters go in khaki shorts (S. Florida swamp) left front. (Strong side for me)
(Although on some days, since I celebrate diversity, I do strong side carry IWB with holsters from Galco) solves that but,..those are larger sub-compacts not technically pocket pistols.
Spare mag goes in cargo pocket right side. Or that little pocket right side for blue jean shorts.
My little Streamlight, (for evening carry), goes in front left (strong side cargo pocket). Car keys in right front. No large key chains recommended.
Cell phone on right side belt holster. Retention at that,...

that covers 90% of daily carry. Except at work... The knife and Streamlight remain but pistola's don't work in Marine Electrical.
It is a routine to get into muscle memory if it suits you. Like grabbing your wallet, keys, phone, etc,...when you leave the house.
Habits can be adaptable. Find a routine that keeps you comfortable and not "fidgeting" at the grocery store. There is a balance, and living in a hot and humid environment 10 months out of the year, you should do just fine in the NW.
Hope some of this helps kick it around a bit.
tw