Trade offs

As I stated in earlier, you have to find the right system that works for you.
You have to find the weapon, the right carry holster, etc in order to ensure that you carry on a regular basis.

Your options are varied and everyone has their own favorites.

You could carry in an ankle holster, a belly band, shoulder holster, in the waistband holster (IWB), etc. Which one of those is right for you? I don't know.
A lot of where you carry depends on what you carry.

If you carry a Glock 19, then your choices are limited, it's a pretty bulky machine and you'd pretty much (although your experience may differ) be limited to in the waist band carry.

If you carry a Roger LCP, then you have more options, ankle, IWB, pocket, you name it.

Remember that for each choice you make there is a trade off. You want the round count and caliber that a compact gives you over a sub-compact and you're going to give up some options on where you can carry it. You prefer the lightweight and comfort of a sub-compact and you're going to lose some of the round count.

The bad thing is that there really isn't a "you can have it all" option out there. Some people will disagree, and that's fine, I just can't see how its possible.

For instance, I thought I was going to go with the Glock 26. It's a great gun, it is a shooter, its ultra-reliable, on and on. The only problem is the dimensions. It's a block of steel, it is bulky and I know that I'd probably not carry it all that often.

So, I'm paring down my size requirement and going with something slimmer and more lightweight so I know I'll carry it. Will I be giving up some round capacity, sure, but only 2 rounds. I will gain, however, a more lightweight and comfortable option to carry consistently.

There are always trade offs in everything. Make the right choice for your budget, body size, clothing options, etc to ensure you carry consistently.