Just got a Galco Jackass for occasional use while driving professionally.

I will be qualifying with it next week, and I'm still a bit weirded out by reholstering it. Pointing a weapon in my direction is freaky.

Any good techniques I should be aware of?

Will the holster break in to the point where I can holster one-handed? As it stands now, the holster would rather push backwards than let the gun slide in. I'm trapping it under my tricep, but it's still taking two hands to get everything fully seated.

Right now, I'm using a draw and return movement where I points the weapon down after clearing leather, then roll my wrist as I bring it on target (reversed for re-holster, obviously), which keeps me from muzzling everything to the left. Don't like the fact that I can't establish a close-in two-handed grip and/or fire immediately on clearing the holster, but this is a special-purpose rig, not an everyday thing (luckily), and if I ever have to draw from it for real, it won't be under surprise circumstances. (There would be a lot of other people shooting while I drive, so if it has come down to me getting a sidearm out, things have gotten pretty pear-shaped already.)