I've been using a Knoppix thumb drive with similar capabilities for years. It's a great tool for imaging systems, adjusting partitions, etc., but it also has a graphical desktop, web browser, and persistent storage. The persistent storage is handled on an encrypted filesystem, so your personal data is fairly secure if you lose the thumb drive and somebody else tries to access it.
I boot the Knoppix 7.2 CD version from a thumb drive, and it works very well. However, I attempted to boot the 7.6 DVD version from a thumb drive a few days ago, and had no luck. I still need to track down a solution for that issue, because I really want to check out the larger DVD image. The 7.6 DVD version has far more application support, including the Blender 3d modeling application, a full LibreOffice install, and some other large packages. I believe it even includes the synaptic package manager for installing any of thousands of other open source apps.
Anyway, the 7.6 Knoppix DVD image might do what you want. I haven't attempted to boot it from DVD yet, so I really don't know what it looks like. The 7.2 CD image boots fine from a flash drive, and may meet most of your requirements. You can grab either via torrent here. If torrents aren't your thing, you can grab the images via ftp or http here.
Info about Knoppix and its siblings can be found here. There are probably a gazillion live distros by now, and you may find something more to your liking here. I stick with Knoppix, because it has served me very well over the past decade. It's not something I boot often, but it is something I couldn't live without. I built my own live disc once. I really liked the flexibility, but it was too large of a project for me to properly keep it updated. Knoppix just works.
dumb question, but when you’ve got windows installed into the VMware, how do you get it from the VMware to a disk or thumbdrive?