Alright, here's and update.
I did as you suggested, and enabled the VPN once in game, all went well. ran it for while with no issues. THEN a new thing happened! instead of simply getting booted to the debrief screen, I got an in game alert window that stated "Mission must be activated." Was unable to use the green end mission button, could use cancel. Might be different since I was running a purchased campaign this time. Ultimately I had to exit the game entirely before I could start that campaign again otherwise I would get the same "Mission must be activated" alert. I had to bail fast (5 month old woke up from his nap) and I didn't think to grab any logs or screenshots. I will replicate the problem before the end of the day however and try to get those data points posted here.
Once I do that, I will likely just run DCS without the VPN enabled for giggles and see what happens just to be thorough.
Also, I'm not above questioning the stability of my system... my rig is... dated. But dated like a rebuilt classic car is dated.
EDIT: repeated the problem as described here. VPN was completely on from the start. Logs should be attached now.
dcs.log