All are valid points. I did extinguish some funds and have a place to do it. I just have to keep reminding myself it's just temporary and will come to an end.
Rifle->pistol->rifle transitions are, in my mind, a lot like doing shoulder switches on a rifle. There's a whole bunch of steps, but once you get good at them, you can pretty much just let it happen without thinking about it. Keep at it, it'll come together. The important thing is to be safe. There's a lot of ways to have an ND during a transition.
One of my Ranger friends actually grabs the handguard of his rifle with his support hand before he holsters his pistol. According to him, this drives urgency in making the transition.
ETA: also, as you've discovered, doing it in full kit with gloves adds to the difficulty substantially. You might consider doing it in street clothes initially.