Initially there was a lot of futzing, because the hardware just came out (UHD 630 Intel graphics). Some things like Nvidia graphics and SD card reader won’t work because of missing drivers, and are unlikely to work in the future.
That said, I use this setup every day and mostly forget it’s not a Mac. I was quite frustrated by the new Touch Bar Macs issued by my work (unpleasant keyboard, no real F keys, USB C only, flimsy back case that has dents in it from regular commuting use somehow), so I didn’t see that as a viable upgrade path for me since I like to keep my computers for 5+ years.
That’s probably not very convincing, but for me it was the right choice. For what’s its worth, I intend to support the XPS 9570 as a Hackintosh platform until at least 2023.
It sounds like you overthink uncertainty, which is something I was stuck in for years. If I just reason it out enough, and have a good idea, and think it all through, maybe I can solve the problem before I quit that cushy job, or so the thinking goes.
It turns out that as long as I'm employed as a factory worker cranking out pointless Jira tickets all day to integrate another A/B testing framework, I don't have any good ideas. Boring works makes people dull.
How to escape: have f-you money. Pay off debts, save ruthlessly. See e.g. Mr Money Mustache [0] or The Simple Path to Wealth [1] for more. Bonus: you'll end up making better decisions at your 9-5 job because _you just don't have to put up with all that_, if the need arises.
My strategy: realizing that having a boring 9-5 job I found unfulfilling would make me insanely unhappy in the long term. You can always get another job if you decide you'd rather do that again.
Did I regret it? Am I happy? N/A. I know for sure I'll regret wasting another day arguing with a project manager that putting a ticket in the "in progress" column isn't actually the same as progress. In any case, others' experience doesn't have any bearing on yours (fortunately!). However, I strongly recommend against discussing this with your coworkers. They've chosen the same path you have, and will demotivate you despite having best intentions for you. If you go on an antarctic expedition, you'll run into a lot of people interested in the South Pole, and may begin to think it's common to spend lots of time thinking about penguins or the aurora australis. Well-intentioned but bad advice is pernicious.
You can't go wrong spending your days doing something that matters to you.
If you haven't read it, I recommend Post Office by Charles Bukowski.