Sir, You list a big range of carry guns Ruger 44 to AMT 380 ? Lots of money being spent on guns holster and ammo at this point in our world. Different guns for different uses is understandable, but in your home state for EDC finding a combination that provides safety, accessibility on your body and fits your hand is paramount. Ive found that people who pocket carry are more likely to "print" and have a more difficult time accessing the weapon when needed. Not to mention the issues of pocket clutter interfering with access and weapon functioning. Pocket holsters are a form of deep cover and can present complex challenges with access.
The other thing is that small guns are much more difficult to shoot well than most gun shop commandos will admit. Liability dictates that we are responsible for every shot fired, both hitting the intended target and unintended. A subcompact or micro pistol seems nice until we see what our individual limitations are on the range, choose carefully only after testing on the range. You may find a mid size gun like the G19 , P320 Carry or P365 XL more to you liking.
The same selection issues apply to holsters, what works for me may not work for you. I happen to like the Askins Avenger style holster as it rides between the 4 and 230 positions well and holds the gun high where your able to cover it with your arm in a tussle. Check out Milt Sparks 55BN holsters. Being new to the CC world you may want to keep things simple at first, don't fall into the crowd that you need to get fancy (complicated), a strong belt holster that positions the gun in the same spot all the time and holds the gun close to your body will conceal. I have an "ever expanding" mid section and the inside the waistband holsters are just not comfortable with mid sized and full sized guns that I shoot well. Also, the best holster will perform poorly without a good GUN belt, not a pants belt. A good belt stabilizes the holster and weapon, holds it in place so you get the advantages of muscle memory under stress.