Well, Galco and Desantis have been making holsters for a very long time. Obviously their holsters are working fine for many people otherwise they would be out of business by now.
My personal opinion is that the Galco owbs tend to close up after a few months which makes re-holstering more difficult but, not impossible. I've not bought one for years so I do not know if that is still the case.
BTW Galco also has a CUSTOM Shop where they will fabricate true custom rigs.
I personally like the fact that I can request a greater degree of cant or a skin shield from the custom makers plus I happen to like the exotic leathers.
So...DO some people spend more & order a custom when a "ready made" will serve them just fine? - For Sure.
Do I personally really appreciate that extra effort concerning stiffer leather selection and minute other attentions to small details? Like how the stitching is ended past the high stress points and the nicer hand boning. I do.
Much of it also has to do with the fact that folks spend a lot of money for their personal self-defense firearms & they want them to live in a super nice house. I know I do.
I also appreciate the individual hand finishing and the confidence that comes along with knowing that I've got the EXACT holster that I want.
Would I die in a gunfight because my "off the shelf" rig had 5 degrees less cant? Probably not.
Heck...this is America. Buy what you can afford and practice with your set-up and for the number of gun-fights you're going to get into in your lifetime you'll be well served.
For me personally...I like being able to call a custom maker up and be able to specify where exactly on a hide I want my personal holster cut from.
Should anybody feel terrible because they don't want to spend more money on a true custom?
No...probably not.
But, if and when you do get the exact holster that you want and your skill level can truly appreciate the subtle differences that make it tailored to you then it's difficult to go back to a production rig.
So for me...even when I contact a custom maker...I don't say: Send me a XXY CoolCarry - I say: Make me a XXY CoolCarry BUT, I want it to have ABCD & add a CDEF and I want it blah blah blah with some shark skin. Whatever,,,,,,,,
For me it's worth it to fork out the extra beans for a custom holster.
For somebody else it might be overkill but, that's fine because I don't have to wear your holster and you don't have to carry in mine.