Thanks for all the input everyone, I really appreciate it.
It's always interesting to see how some people equate being new on a forum to being new to firearms. I assure you the latter is not the case. My reasons for considering .22lr in a CCW have nothing to do with being shy of larger calibers.
As someone correctly guessed, with my job and all the stuff I'm carrying around with me, it just isn't realistic for me to always have speed strips/loaders, moon clips, or extra ammo with me. Which is why capacity has some extra priority in this decision. I'm not an idiot though, I've been shooting both 9mm and .22lr about half of my life (I'm 22yo) and I'm well aware of the advantages of 9mm over .22.
Well, right now I pocket carry a .38spl (S&W 642) and although I love it and it's pretty wood grips, I'm trying to minimize the calibers I have to buy for, and since I have 3 other firearms in 9mm it just makes sense to trade in the .38 towards an LCR in 9mm; it's one less caliber I have to worry about purchasing and keeping stocked. Plus the moon clips are nice
So with that in mind, my current plan is to sell the 642 and put the money towards an LCR in 9mm. I'll keep a reload or two in my truck for my peace of mind, even though the odds of me ever having to reload (or the chance to reload) in a self-defense situation are very slim… It can't hurt. Maybe at some point I'll get an LCR in .22lr to go with it and keep in the truck as a backup, but for now I think I'll get the 9mm.
My next goal is to start reloading, I already have plenty of experience helping my uncle crank out .44 special in his basement, but I'll have to sell some stocks to get the equipment. I'm tired of paying ridiculous prices for ammo.
Thanks again for sharing your thoughts!