Your set up, IMHO, should involve as little unholstering/reholstering as possible. The more you handle a firearm, the more opportunities for mistakes...
While driving for Uber since February, I have gotten out of my car twice to help someone with bags. If that situation arose, I would likely expose the firearm in the least conspicuous way possible. I could get out when they are out of the car and close my door behind me or temporarily unholster and put it under my seat...
Professional self defense instructors recommend on body carry. A plan to be transferring your firearm between locations in a vehicle is poor planning. How do you do this discretely without pointing the gun at yourself or others? Unnecessary gun handling such as unholstering//holstering is a huge factor in negligent discharges. Let alone the mentality of knowing (or wondering) exactly where your gun is at all times.
Josh, you don't have to wait for your license or the gun purchase to start training. Any instructor should be able to provide a gun and gear to train with as long as you specify you need them to. You will likely need to coordinate on what ammo to bring.
I'd suggest to start training as soon as possible. This will help with making lots of decisions on guns, gear, habits and mindset. It might actually save you money in the bigger picture, avoiding going in bad directions on all of this.
There are lots of top notch local trainers right here on INGO :
https://www.indianagunowners.com/forums/tactics-training/
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