To be realistic: Windows and MacOS are both great for getting "real work done".
I've never had an issue with this "35 character file save prompt" limit, and I cannot imagine it would be a dealbreaker even if I did.
Telemetry is irrelevant to getting "real work" done, assuming its implemented in a way which doesn't impact performance, and I've never had an issue on Windows. What you're talking about is privacy concerns, which are very, very legitimate; and have nothing to do with "real work".
Some things are more productive in Mac, others are more productive in Windows. I'll die on this hill: Microsoft Paint is a top 5 productivity application for me. If I need to quickly take an image, layer a second image on top of it, resize, and add some text; there's nothing more productive than Paint for that. The result looks like shit, but its productive. The ability to hit Win+Shift+S, screenshot a part of the screen, then immediately paste it somewhere? Huge. MacOS has nothing like this; it has all the same basic tools, but they don't tie together to enable the same velocity; even the screen clipping tool takes like 5 seconds for the image to leave the screen corner and hit the filesystem. Notepad is another example; I open notepad and can immediately start typing. On MacOS, I can open Notes, CMD+N to get a new note, it defaults to formatting for the title but at least that works; or you can do TextEdit, and you're presented with a "create a new document" dialog; no thanks. Little moments which add up.
But where does MacOS pull ahead? If I need to edit a video? Windows has nothing for me; maybe DaVinci, but its hyper-pro level tooling. iMovie is great, and years ago I splurged on the buy-once-and-done FCPX subscription: its fantastic. Photo editing beyond what Paint can do? No, I'm not paying $200/month for Photoshop; maybe you can try GIMP, but I'm using my $20 og Pixelmator purchase from a decade ago, it works great (ugh I guess I should support them and buy the new one). All the UNIX tooling of course. Need some light CAD? I love Shapr3D; and I'm super happy to see its coming to Windows soon, but traditionally its been an Apple-only thing. In short: MacOS owns Prosumer-tier software; Pro-Pro tier stuff tends to be on Windows+Mac (like, Adobe), but there's a ton of cool software right below that which is Mac-only.
Linux is the one OS where I have broad issues getting work done. If I'm developing a website or a web app? Sure, it works as good as anything else (better than Windows to be fair). But go beyond that and there are dragons. A juxtoposition of trying to make mediocre web apps or libre software work for workloads which should be native. CAD? No Fusion360, no Shapr3D... Tinkercad I guess? Vectary, kinda ok. LibreCAD, I'm sure was productive in 1997. Spreadsheet guru? Calc & Google Sheets have come a long way, but they're still in another realm compared to Excel; but I'm a big personal fan of Numbers, as it doesn't try to be Excel and instead serves a slightly different kind of user.