I reboot every 2 months or so.

I often keep e.g. games suspended, especially when they are slow to start or have poor savegame support. I minimize them and suspend with process explorer. End user triggered savegames have had declining support for years.

I also don't particularly enjoy re-setting my screen session just the way I left it. There's a reason I run screen; it's persistent.

I stop the Windows Update service on a loop, because (on Windows 7 at least) it's quite buggy, eating hours of CPU time at 100% on a core, and stopping it once isn't enough.

I don't do any real work in Windows any more. In many ways, that makes it more annoying to reboot, because less perceived uptime has been had.

For me, it's because I hardly ever use my Windows partition. What happens is that I boot it up once every few months, and then Windows Update immediately has a panic attack and starts downloading vast amounts of stuff behind the scenes and harassing me about reboots --- while I'm trying (and frequently failing) to get work done.

I really want to turn the automatic updates off, because they are actively counterproductive to everything I want to do. I know I need to update it, but I'll update it on my own schedule, thanks (like, when I'm not actually trying to use the computer).

At this point I no longer trust Windows Update to do its job properly. The idea of it even thinking about forcing a reboot terrifies me.

I'm not OP but sometimes I'll do a high def video render that's only practical to run overnight. If I lose several hours of processing because Windows decided to reboot itself somewhere in the middle of the night I won't be a happy camper.