I still don't have my CHL, still putting together some finances towards it, but I have done quite a bit of research. Holster wear and gun wear aren't the reasons behind differing EDC's. Seasonal weather and clothing options and quite frankly, just how you feel about the day are the different reasons behind having more than one EDC option. Are you going to the beach where clothing is minimal? Take the Kahr PM9/CM or CW9/XD9SC/LC9/insert small CCW type weapon here. Is it going to be a shorts and t-shirt type of day? Same as above or maybe a little bit larger but still a compact handgun. How about heavy winter weather? Maybe a larger full size weapon. Of course, I see other posters all the time saying they they wear OWB when the weather is heavy Winter. I always wonder, don't they have to take off those parkas at some point? How does that leave their OWB then? Pouching way out on one side is how I see it. So, I keep thinking, for the weather we have here in the DFW area, IWB is the way I think I'm gonna go.
In any case, it's kind of up to you. If you have the funds to give yourself options, then by all means set yourself to cover the different possibilities. But don't do it because of holster wear or gun wear. Kydex holsters do loosen up over time I have read. Just put your handgun back in it and heat it up with a blowdryer. It'll go back into place.
My .02 worth.
May you have good, safe shootings.