

Sounds like you’ve got a good handle on most of it. FWIW, here’s how I deal with some of the same issues:
For Windows apps I’ve found a virtual machine is the easiest solution. It’s set it up to share folders between Linux and the Windows VM so moving things between OS’s is easy. I’ve tried other methods like Wine, and for the Windows apps I need the VM works best by far.
Did you mean Timeshift? (Time Machine is Apple software.) Timeshift works great for incremental backups and is easy to use so you should get it working, but in my case I also do full system backups every few weeks because setting up my systems from scratch is a PITA and really time consuming, especially for my server.
For those full backups I’ve set up a bootable persistent live USB SSD with Ubuntu. The persistent SSD is fully configured with all software, including VNC, SSH and Clonezilla. Creating a backup requires plugging in the SSD, rebooting and running Clonezilla either locally or remotely. Clonezilla is also also preconfigured so it requires only a few steps to start the backup. Full system backups take about 20-30 minutes to complete but my SSDs aren’t that big.
Enjoy your move to Linux. It’s well worth the effort.
I started with a Clonezilla USB a few years ago, but Ubuntu is more flexible and can be used for everything with both VNC and SSH. The GUI is easier for some tasks, and Nautilus, Disk Usage Analyzer, Gparted, and other utilities are all available on the same SSD used for backups.