But if you don't trust Tor more than https, when are you using it?
If you want to create a secure connection to your office, I think the best tool to use is VPN.
I'm not sure what kind of trigger you're looking for, but I'm sure that you could write a script that will make it happen.
I agree I don't use tor for anything I type a password into. I use tor for random untrusted webpages only. Sometimes I just use tor to compare a key or cert, a trick I learned from Qubes forums.
also I should add, they have new feature to update with tor. but I also wonder how better that is because it seems to me tor is attacked with fake keys more then anything. And all it takes is for the user to hit y one time.
I can count dozens upon doznes of times i had to make sure i hit n. and kept trying till I got a verified key. I've mean i posted so much about it on whonix I pissed the guy off. not just wrong keys but servers going out. But I can only count 1 or 2 times that happened through my regular connection.
I don't let my family update dom0 anymore.