I'll probably never "get it right" since even if I have a great holster, I'll no doubt see something else that looks like it will be better than what I have right now.
I think this pretty much sums things up in the real world.
Holster design and options have progressed, and continue to progress at an amazing rate, and what was available and "the best" just a few years ago, has since been outdone ten fold today.
If youre serious about carrying, its going to take some hands on work to know whats really going to work the best for you. Thats really the only way to know. This is usually where "the box" comes in. Things that look good in theory, often tend to not work out as well in actual use, and the box begins to fill.
All that goes on with just one type of holster too, so for each different type gun, and use, and placement of carry, the number of holsters just multiplies exponentially, and the box gets bigger, and your wallet thinner.
The plus side to all of this is, you usually end up finding things that work best for you, allowing you to focus on one or two models for each type of carry, and you settle in. Well, at least until the next round of the latest and greatest shows up.
One saving grace I found a number of years back, was EBay. I found it was a great place to get rid of my "boxes" and recoup some of that money. I also found it was a good place to buy lightly used brand name holsters at reasonable prices if I saw something that looked promising.