I'm switching the machine controlling my Offline wallets... But it simply doesn't get out of offline mode
Just nitpicking
CalledProcessError: Command '[u'icacls', u'D:\\Bitcoin\\bitcoin.conf', u'/inheritance:r', u'/grant:r', u'*******:F']' returned non-zero exit status 5
It failed to change privileges on bitcoin.conf, most likely because you user doesn't have the proper credentials to change access rights on that drive.
There are a few solutions available:
1) Start Armory with admin rights (I don't recommend this)
2) Turn off auto bitcoind management and run BitcoinQt yourself.
3) Start Armory with --disable-conf-permis (
https://github.com/etotheipi/BitcoinArmory/blob/master/armoryengine/ArmoryUtils.py#L120). I don't exactly recommend this either
4) Give your user the proper permission. Right click on the D drive, go to the security tab, pick your user and give it full control over the drive.
5) Move your bitcoin folder into a path your user has full rights over (most likely C:\Users\*yourusername*)