Status update for anyone having similar problems: This issue was kind of entirely my fault - but I would have never guessed it in a million years.
The deep hibernation cold issue was caused by having ESPN set as the homepage on the internet browser. Apparently, having it constantly refreshing scores in the background while the car was off and charging caused the computer to shut down after a while. There was no mechanical issue. Now that a more static webpage is set as the homepage everything appears to be fine.
I didn't know enough about web design/tech to realize this could be the problem - and Im warning other users who may not be web savvy either.
I can't imagine they haven't thought about this before. I stream stock quotes very often in my car. Hope they fix this before they get mainstream as many people will have this problem. Tesla is an amazing company but on the software side they're lacking a little bit.