I disagree with the premise that a gun has to be a pocket/pocketable gun to be a true CCW pistol. I disagree with the premise that larger guns are OK in winter or cooler climates, but are not warm-weather CCW pistols. Heck, that second part really makes no sense to me. I like IWB carry (tucked or untucked). If you are working in a professional environment the only difference between business dress or business casual during the cooler months v. the warmer months is you are less likely to wear a blazer/suit/sport coat so you would need a tuckable IWB over a regular IWB or OWB or you may wear short sleeves in the summer which would have no bearing on how you carry. When going casual, with an untucked T-shirt, sport shirt or polo with shorts, jeans or khakis/chinos you can carry whatever you want so long as it isn't too thick or the shirt isn't too tight, and with a tucked T-shirt, polo or short shirt most thinner double stacks and pretty much any single stack will work with a tuckable IWB. Before you say "you aren't in TX/FL/whatever", MD summers do get pretty hot. Highs in the 90's is the norm this time of year, and we get 100+ degree days most summers (usually a nice string of them). Our humidity can rival much more tropical regions this time of year (with all the rivers and streams, the Bay, the ocean to our east, and mountains to the west keeping it all contained, and being in the northernmost reaches of the subtropical zone, it gets quite humid). In fact, a friend from FL who is just experiencing her 2nd MD summer is convinced it is more humid here than where she is from, and almost as hot.
That said, the OP prefers pocket carry, so consider pocketable guns. No pocketable gun will be a good gun for everything. If it is small and light enough for pocket carry, it is too small and light to be a do everything gun, not much can be done about that. However, some are closer than others.
If I was him, I'd steer clear of the lightest weight 9mms. The recoil will be pretty stout and that will make it difficult to have quick follow up shots, and in all likelihood the amount of range time will suffer as well. A 20ish oz gun may be heavy for full-time pocket use, but it is pocketable. Getting something in that range with both an IWB (preferably a tucked IWB) holster and a pocket holster could be a decent full-time/all scenarios carry gun if you just want one. With a good IWB and pocket holster, the heavier single stack/micro 9s are as close as you'll get to one gun that can do everything if you want pocket carry.
My SIG P290RS is quite accurate and comfortable for its size, and the cloth on my chinos/khakis and jeans are substantial enough that it doesn't print (it won't work very well with very thin dress pants and suit pants though). Guns that seem to be a similar blend of range comfort/accuracy and size are the Shields, PPS, SIG P938 and there are others. Personally, I've also shot the Kahr PM9 and MK9 and I can vouch for the MK9 being quite comfortable and both being quite accurate for the size. Another option could be an all steel J-frame if you don't mind the capacity.
