Word

OP, I know I'm a little late to the party but here's my answer:

Crossbreed Supertuck. I bought one for my Sig P6 after reading numerous other people on the internet state that they were very comfortable holsters for IWB. Numerous reviews on defensivecarry . com swayed me in that direction.
Tommy Theis holster. It's very similar to a Crossbreed Supertuck but the wait time was less than Crossbreed and I wanted a holster without a long 6-8 week wait like Crossbreed had at the time. I CCW my Sig P220 in it and it's just as comfortable as my Crosbreed.
Some generic leather holster I picked up at a gun show. I don't like it. It holds my CCW secure-ish but it's not blocked and molded to that pistol so I'm not content with it. I CCW my S&W M&P 9c in it but it'll be riding in another holster before too long.
Foxxholster. I ordered this for another pistol I have and plan to make it my primary CCW. Reports on the holster according to the internet are good and it's a comfortable holster. It's similar to Tommy Theis and Crossbreed Supertuck but approximately $20 less and shipped 1 day after I placed my order. If it's sufficient, I'll pick another one up for my M&P 9c and use it as my summer carry. My FNX 45 will be my winter carry.

As a lefty, I tend to carry my pistol IWB and just behind my left hip. Call it 8:30 or so. There are times when I carry at 9:00 but it's usually because I've had it on all day and it's starting to jab me or I wore the wrong pair of jeans and they're binding in some way. I haven't tried carrying with my pistol at 10:00 or even 11:00 and don't plan to. It just doesn't sound comfortable to me and would restrict access to my left front pocket where I keep my pocket knife and cash if I have any. I carry my wallet in my left rear pocket and the holster at times can interfere with my whipping my wallet out if it's too far back like at 8:00 or even 7:30. That's also why I wear my holster where it is so it interferes minimally with this.

I don't carry a flashlight. I don't plan on it either. I also don't carry an extra magazine but am beginning to heavily consider doing that because the way the world is going. When I get one, it will most likely be a kydex mag carrier and I'll carry it on my right side just forward of my right hip at say 2:30. 3:30 might contribute to wear on vehicle seats and I want to minimize that. Speaking of which, I make a concerted effort to not rub the bolster of the driver's seat with my pistol when I'm carrying.

I'm 5'11" and around 185# give or take. I wear size 32 pants and don't have a true gun belt to go along with my holster. The one I use works fine but I will pick up a designed to carry leather belt. I don't wear jeans that are 1 or 2 sizes larger to allow for more space my weapon. It does not result in my jeans being extremely tight or uncomfortable. I do have one pair of jeans that is just tight when it's just me in them so I don't CCW in those... and I need to lay off the ice cream.

You made a good choice in Crossbreed. They're known for quality products that do what they say they will comfortably.

This!  On the rare occasion I don't use my TT Gunleather I use a comptac mtac.

I have one of those for my Hill People Gear chest rig.

For kydex, I make my own.  Made this for mah p07


I have a leather Galco glock iwb that gets a lot of mileage also.  It's just handy.  It also fits just about anything, somehow.

Ian Martin at International handgun leather.  Quality is top notch.
I have another one on order right now. It's the Ultimate Trojan.

Just sold my Comptac Minotaur for a Stealth Gear Onyx, most comfortable holster I own.   It doesn't get soaked in sweat like the leather ones do.

I use this.

It is, hands down, the most comfortable holster that I have ever used. I don't even bother with my OWB holster anymore.

Sorry! My experience of carry all these years probable can not help you.
You may all ready know the answer: Looks like a lot of this is very specific
to an individuals body, their build, their climate, etc.
Maybe others have told you, But it is mostly trial and era.
For me when I stated to CC I know about where I want the gun to ride.
So I bought the First Pistol Pocket IWB holster from Bianchi. Do ask the year.
I see that this style of carry wont work for you. So you have an even harder job.
Because I know (yes I had to try it) where I wanted the gun to ride, I never look back.
Now that does not mean I did not try other holsters. I just all ways came back to IWB.
I have modernize went from leather holster to Kydex one. Belt is nylon as well.
But still IWB.  Carry spare mag/ ammo. I sure do. Hopeful my gun will run fine, if I need it.
But if I run out of ammo or the magazine brakes, I have a expensive club. Mags are OWB.
Got enough on the inside,
All of this is IMHO. Sorry no quick fix.
And for the part: forgotten the rather confusing process of trying things out!
No I have not. I have a box in the closet full of holsters that worked as well as some that did not!
One last thing Clint Smith who knows a HELL of a lot more then me. Always says carrying a
gun should be comforting, not necessarily be comfortable.(Yes there are time Mine is uncomfortable)

Good luck! Doubt if any of this has helped.
Let us know what YOU found that worked for you!

PITA45

Comp Tac MTAC at 3:30(ish), spare mag in a Comp Tac mag pouch, AGC bullhide belt.

Milt Sparks, Raven Concealment, + T.Rex Arms.

Theis at 430. SW shield.

Nothing else came close. But for me the gun was as important as the holster. My theis/g19 concealed better than mtac/xds.

I'm 6'6",235. 38x36 pants. Have to wear tall shirts or they ride up on the butt of any gun.

I'm rather small myself and I carry using a Stealth Gear Onyx. Super comfortable.