I may replace my Glock 19 with a SIG P365 Macro

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I have P365, XL, and Macro. Also 3 G19s, and G45.

My journey ended up with swapping slides between the XL and the Macro and carrying the XL with the 17 rounder as a reload. Just enough to get a full grip, small enough that is still easily concealable with a dot and TLR7. And I thought the compensator was gimmicky, until I fired it.
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I have a 365XL with a Wilson Combat grip module and I just a few days ago got a chance to try out a Macro that a friend just bought and I'm happy to stay with what I have.I also have a 365,well um,I mean my wife has a 365 and it's a little small feeling to me but I can still shoot it ok.I also have a WC module for a 365 so I can carry my XL with flush fit 10 round mags if I really need to hide it better.When I was shooting the Macro I was also shooting my 365XL,and I was shooting at a BC-27(hope I got the number right)target and scored a 48 out of 50 at 40 yards.I've shot my XL a lot and it doesn't shoot like a small pistol at all.A 48 on that target is hard for me to do with my P210 on a good day.But I think we all have a pistol that fits and shoots better than others,and for me it's the 365XL the way mine's set up.I carry it with a factory 12 round and have a 15 round in the holder on my belt.It's an efficient little setup that's really handy to carry and shoot.
 
Your very, very long post sounds like the internal dialog I have in my head all day while brushing my teeth, driving to the job, working on the job, driving home from the job, shower, laying in bed, this gun, that gun, this one has this but the other one has that, but I have this one thats kind of like the one im looking at, etc....:D holy crackers man. I feel your pain, I do all sorts of mental gymnastics and spend a long while making up my mind when I am trying to make a purchasing decision....
 
Update:

While I may revisit things later, I'm not going with the larger P365 (either the XL or the Macro). I may eventually add the XL with 17 round mags and a mag adapter to be a larger P365. However, I shoot the P365 well enough that any improvement due to the longer sights will be pretty marginal. Similarly, modern 9mm JHPs preform well enough out of a short barrel that again, any improvement will be marginal. I will buy a couple 17 round mags with grip adapters for my regular P365 for the capacity improvement when I'm dressed to conceal it (and to carry as reloads the rest of the time), but buying the P365 Macro or P365 XL is on hold. For now I'm going to focus on other acquisitions.
 
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