Long time Linux user being forced to use Windows occasionally...I don't know how you folks stand it. It feels like every time I boot it I get half dozen notifications, ads disguised as security, telling me I need to restart now even though I just booted it. Maybe it's my own ignorance, but wow.

Outlook is a killer application, I agree. The web version is actually pretty useable IMO, so much so that it's all I use anymore. Evolution is an open source Outlooky application that I used to use and does work quite well, if you prefer native.

Printing to Dymo should be possible, I did a cursory search and a few people seem to have gotten it to work. Won't be as straightforward as Windows, I'm sure.

I think the biggest thing missing in Linux is Excel, which luckily I don't use or need to use these days. The LibreOffice equivalent is nowhere near as easy to use IMO. Anyone who uses Excel heavily I probably wouldn't promote Linux to.