I've paid for a lot of software that can't run on Linux, but I feel like I've gotten the value out of most of them. In theory everything I do either works in Linux natively or has a Linux equivalent. I just haven't tried any of it on modern hardware to know if it'll actually work.
> Have you considered a Hackintosh? And what's keeping you off of Windows?
Most of the reasons for switching to Linux are related to OS/security/privacy/automation tweaks that I haven't been able to make work (or work reliably) in Windows/OSX. I have all that stuff working in Linux today, but my hardware is too out of date to do the bulk of my work on.
Honestly, I could probably spend some time in mastering powershell, and educating myself on the current state of Windows and maybe do everything I want, it's just not something I'm interested in doing.
> Consuming media through the laptop is another sticking point. I had tons of bizarre issues with Chrome/Firefox and streaming video sites. It was just a mess.
This has been my experience as well, but I'm also on 7 year old hardware.
For the last ~12 years I've been on OS X. Before that I was primarily Slackware user. I switched to OS X when I started doing a lot of A/V work (at the time working with SDL dependencies was kind of a mess).My Air is dying and I'm considering purchasing one of the newer Skylake-based 4K laptops to run Arch, rather than shell out $3k for a $1200 notebook. (It's a value thing, not a cost thing....
If you're planning on sticking around (and your manager likes you), see if you can work with them to tweak your title before the deal goes through.