ESXi, WinToGo, and Other Virtualization Questions

I have a concept in my head, but I'm unsure of the best way to complete it. For work, I use many different computers of varying hardware configurations, age, speeds, etc. so most of the work I do has to be portable. WindowsToGo is a great solution for this, and I've got a WTG drive that is both bootable and can be run in VMWare if needed. I'd like to get this drive synced to an ESXi server as well. I have physical access to the server from home and can plug in, and would like to have it pull the file and update the ESXi VM when I do so.

To make matters much worse, we use Easy2Boot, a version of Grub4Dos to boot multiple different ISOs. This would require the WTG installation to be packaged into a partition image fine (.imgPTN).

Goals:

1. Boot directly from USB

2. Boot USB as VM

3. Contain WTG in an E2B drive, while retaining both 1 and 2

4. Sync the full VM to an ESXi server and have the ability to run it remotely.

I'm well aware of solutions like Dropbox, Drive, Github, and other ways to sync files and folders. I'd like to have 1 single environment, located on both my USB drive and the ESXi server. Any help is appreciated.