I honestly don't even know how people have enough motivation to dual boot windows - you essentially need to maintain two full sets of your communications and browser stuff, where one is updated automatically, and the other ... well yeah, windows is fucked up. And the few games I can't play are shit anyway.
I don't see why it would be that annoying. I use Firefox on my phone and desktop, and things sync just fine, so I don't see why throwing Windows into the mix would matter. LIkewise for things like Discord, you just login and you're good to go. I guess if you install something in one place you need to do it in both, but that's a one-time thing.
For me, the most annoying things come from the Windows side. Windows likes reboot during updates, and since my default is Linux, the next time I use Windows it inevitably needs to reboot a couple times before I can do anything. That's a really crappy user experience, especially since I only boot into Windows like once/year. If I used Windows more, it would be less of an issue.
Keeping stuff up to date on windows is certainly more annoying, the more programs you have. And if I wanted to replicate my Arch setup in the slightest, so I could even use it, it would be hell.
I did it for about three months while I was getting used to Linux and I have a machine that I share with a Windows user so dual boot is necessary and for a while I was gaming on Windows and coding on Linux which was on an HDD but we got an NVMe SSD and now Linux is on there so gaming is no problem.