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The following is all said with the understanding that what I like...you may hate...and vice versa.
While it would seem that OWB would beat IWB in comfort in every way, I don't find it to be so. Sure, you have that metal shoved down your pants, but there's more to it than that. Comfort can be affected by many things.
1- When I carry OWB, I find the gun bangs into more things- door frames, elbows, chairs (especially chairs). Having most of the gun pinned under pants keeps that much of it secure and protected, and the rest of the gun is held close to the body by the nature of the holster.
It's very rare that I "bump the gun" when carrying IWB.
2-The weight is spread out more with an IWB holster. It's usually said that an OWB holster is supported by the belt, and is dependent upon that belt to hold the weight. I believe that some weight is also supported by your hip as the holster is pressed against it.
I think the IWB spreads the weight better, because it is basically supported on all sides.
3-Some don't like the gun/holster to shift around. I don't mind it so much, and actually like a little movement so the gun moves with me just a little bit.
I think IWB holsters hold their position better since they are "pinned" between you and your pants. Some might say the OWB has more tendancy to "flop out" from the body, but a proper belt will fix most of that.
Myself- I carry a Govt-size 1911 IWB (Sparks Summer Special) all day, everyday. I put it on when I get up, and don't take it off until bed.
Now, your questions in order:
1- I'm smaller than you, at 5-8/180. I have a back injury also, so I whine about anything uncomfortable.
2-Not having carried in a few years, you'll probably find any mode of carry awkward at first. I lived in a non-carry state for seven years, and when I moved back, got my permit, and started carrying, I thought it was clumsy and heavy...even though I carried before for several years.
You'll just have to give it time. It's worth your while.
3- You might carry it more than you think. I used to carry off and on. I found it easier to carry it all the time. It's better to get used to it than to feel like you're carrying for the first time each time you do carry. You just get used to it, and it's better to know it's there all the time.
Coming home and walking into a break-in one day when I DID have a gun also convinced me to always carry.
4- I use the same holster for everything, but some will have a dedicated "car holster". When they get in the car, they put the gun in that holster. But, when driving, I have taken my "backup" out and located it for better access.
Check local laws, etc.
5-A P226 should be fine if you do carry IWB. I carried a P220 quite a bit, which is about the same size. The 1911 I carry now is a bit bigger overall, though it's a touch thinner.
6- I'm in the Midwest also. Another plus for the IWB- it works with every season/type of clothing.
I used to change carry modes with the weather, and even changed guns- I would carry a full-size gun in winter and a smaller one in summer.
I don't know when I did it, but at some point I realized that I had gone to IWB and full-size gun year-round. Things are a lot simpler with one gun and one mode of carry.
If I have to wear something that won't allow the 1911 to conceal, I will change guns. It doesn't happen often, but it can happen with some clothing. I go to a smaller gun, but stay with an IWB holster, in the same location.
My favorite IWB holster is the Sparks Summer Special (although I got an older Alessi Hideout for a HiPower recently that I like), and my favorite OWB holster is the Alessi CQC/S.
I consider IWB holsters to come in two basic variants (these are my defintions only, others may hate them)-
Narrow, like the Summer Special and Alessi Hideout, with the belt loops close together (or just one loop) and a minimal amount of leather in the holster.
Wide , like the Sparks VersaMax 2 (VM-2), with widely spaced loops and a broad holster body.
The wide IWB holsters are meant to do two things- spread the weight of the gun, and put a loop at each end to make it more stable.
The narrow IWB holsters put less material into your pants, and the narrow loops may be the best choice for small-waisted people who don't have a lot of belt space.
I like narrow ones. It's less to shove in my pants, I don't find the width to be needed to support the weight, and find the wide spaced loops TOO stable.
OWB, I like the Alessi CQC/S. It's the king. It's amazing how stable it is, and the fact it's done with snap-on loops is even more incredible. I prefer IWB, but I also have a CQC/S for each gun I carry.
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