I want to carry, but...

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Yes, I think a sub-compact may be the way to go for me. Smaller profile, smaller holster..., we will see. I’m actually considering the Sig 365 as my next, and try that for my carry option.

Late to the thread. I read through most of the thread. I have recently purchased a P365 and it is quickly becoming my favorite CCW. Due to my lifestyle/dress I favor pocket carry but I understand that does not work for you. As many have said, in terms of comfort OWB is more so than IWB.
The only real disadvantage to OWB is that your weapon will print a little more than IWB. Some OWB will print more so than others. In locations that printing is not so much a concern for you then try carrying that method. What works for me I fully understand may not for you. Pocket carrying a P365 for me is by far the most comfortable. I wear pants with roomy pockets and the pants are not a tight fit but have a little comfort room. Some will say that gun is too large for pocket carry and for them they are correct. There are others like me that it works fine for. I even pocket carry with the 12 round mag. I do totally understand and relate to comfort issue but as one well known Gun Instructor says, the gun is not meant to be comfortable. It is meant to be comforting. So, that is to say there will be some degree of trade off for you. The trade off between comfort and comforting and only you can decide where the balance works best for you. I hope you find the combination that is right for you.
 
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I have yet to find a comfortable carry option that works for me. No matter what I try, either my gun, or holster set up digs into my body such that it is so uncomfortable as to make me give up. I’m not going to purchase a fourth carry option until I know it will be comfortable.

So far, I prefer behind my hip, but not in small of my back, drawing with palm away (knuckles against hip/back). But even with this, the set up digs into my skin and I just can’t get comfortable. I now carry in a small backpack that goes everywhere with me. I know that isn’t ideal, but for me, it is better than nothing.

For those who can relate, what can I do to increase comfort so I can carry. Appreciate any help.

Try a pancake type holster and a small gun. You need a good belt too.
 
Ruger LCP in a Sneaky Pete (with an Apple logo sticker on it)

OWB carry that's hidden in plane site.... I've worn it everywhere and have never had anyone even look twice at me.

The key with this rig is to limit yourself to the smallest holster Pete makes. Any of the rest are awkwardly too big....

But mine looks just like a cell phone case.
 
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