That is one of the great things about training. You get to test your ideas about reality against actual reality. That particular gear set-up for my pistol is one of my ideas that didn't fare as well against reality.
My thinking at the time was that I wasted a lot of time either getting ready for the firing line or making myself look presentable so I could run into town for lunch/what-have-you. I decided I wanted a single set of LBE that had everything I needed for training on it that I could easily throw on. I also liked the idea that I could have this set up around the house and have everything I trained with ready for a defensive scenario. This meant having a pistol on the chest rig.
At the same time, I wanted to keep my CCW pistol (which you can also see in the pics) because it made finishing for the day as easy as taking off the chest rig and putting on a cover garment.
It seems to me it would work better under the left arm, butt to front, same as a standard shoulder holster.
There are several reasons I chose not to even consider crossdraw when I decided to mount the pistol on the chest rig:
1. It would involve training a whole new set of muscle memory for pistol draw that was substantially different from what I had been training for 5-6 years and tens of thousands of rounds at that point.
2. I train to keep control of the rifle muzzle during transition by tucking it under my weakside arm or holding it with my weak hand. Because the rifle would be covering a crossdraw holster, I would either need to convince my instructor to change his curriculum or I would have to try and dig the pistol out from underneath my rifle. I would also have a hard time not sweeping myself during the draw as a result.
3. Because this training is conducted with multiple people, I would also be sweeping everybody to the left of me with a loaded pistol during every transition. Naturally, the instructor would not have let that happen even if I had been willing to try it.
Is there a specific reason you have it set up that way?
It is set up that way; because moving it slightly forward keeps it from banging against my CCW piece, which I was also wearing (for convenience sake and because I kept reaching for my CCW piece out of habit). It is up slightly higher because the MOLLE attachments for the holster start around where the trigger guard is - so if I mounted it low enough to be comfortable, it would basically be attached by a single MOLLE strap and be obnoxiously floppy during movement (not to mention pointing at my lower anatomy frequently).
In that position, I basically use the same muscle memory as I do with my CCW piece, I just pick up the pistol in a slightly different spot and I have to extend up a little more. In the end, that didn't work as well as I would have liked and I mounted the holster as low as it would go and then secured the top of the holster to the chest rig with zip ties. That solved the flopping problem and made the holster easier to use.
Currently, I still have my chest rig set up that way; but I rarely carry the pistol on the chest rig anymore. I've gone back to using the belt rig (though I haven't been able to do much shooting of any kind in the last year). What little time I saved going to and from the range was more than burnt up by having to unload/make safe and load/make ready three different pistols while going from the firing line to the schoolhouse and vice versa. In addition, I continued to try and draw my CCW, so despite the similarity of muscle memory, it wasn't working for me.
The only places where that rig was really handy were when we did the vehicle stuff. The chest rig holster was a lot easier to draw from and get into action while sitting in a vehicle with your seatbelt on.
Right now, I am rethinking the chest rig entirely. I like chest rigs and they have a lot of pluses - not the least of which is that your magazines are right where they need to be for economy of movement; but there are some advantages to a slicker profile too.