Ksail, great post, please keep them coming. My vote would be for you to keep posting, not PM's, the sharing of opinions is what makes a forum work. If you decide to PM, please put me on your list.
My wife and I are contractors, and since most of our day is in someone's home, carrying is not an option. I'm also left handed, and that's another problem in a vehicle. I've been looking at off body carry, combining it with some sort of mini BOB (bug out bag).
I've tried soft briefcases, different kinds of bags, and backpacks. Nothing seems to work for me. What I'm looking for is something with lots of pockets so I'm not just dumping a lot of stuff into a big bag. Also a separate pocket for the gun, and can be carried like both a briefcase or backpack.
Since my truck is a full size van, taking the gun out and putting it into a IWB holster unseen is not a problem, and the ability to pull the gun out of a bag with my right hand is a real plus.
One embarrassing story;
I was doing a lot of wheelchair ramps in the inner city, and had an aluminum clipboard with a compartment for storing forms. I decided that compartment would be a great place for a gun. I cut out the profile in wood, and lined it with felt (glued in place). After allowing the glue to dry a day, I put my Colt 10mm Delta Elite in it. A couple of days later, I opened the case and there was my beautiful gun all rusted up. Apparently the glue hadn't completely dried.
Anyway, I think off body carry is something we all might have a use for, if we could find a way to do it. Maybe a "manbag" (just kidding, I got enough comments about my choice of text colors in the chat room

)
Thanks again,
Art