Ask HN: Finding my place as a developer

I am currently a sysadmin but finishing up a degree in programming and planning on making a move to development which has been what I really wanted to do since for decades I doubt I'm the only one who has ever been in this situation and I'm hoping for any advice. On the one hand, I like FOSS, on the other I feel that, from a more practical standpoint, systems like Windows and macOS make more sense. I like the cohesiveness and polish they can bring as well as less workarounds. My MBP died last year and I’ve been using Linux (using Linux since the 90’s) but am strongly considering another MBP (stupid touchbar is holding me back). Linux is fine, but I personally think both Windows and macOS just look better. So, first question is: how does one really decide which is more important? Software freedom or convenience/usability/etc. For instance, know Windows has telemetry and the updates suck at times but there are workarounds and besides those, I like Windows 10. I've always read that developing on Windows supposedly sucks, but I don't see an issue. Maybe because most of what I did was contained in MS ecosystem. My second question is related to the first. How do FOSS advocates who are devs deal with the reality of developing in the real world where there's a good chance they're working with closed systems? My thought is if I'm working on all in-house stuff, it's irrelevant anyway. But, what if I ever move into something that develops for clients? Final question: How does one know where they belong re: startup vs corporate? On the one hand, I like the freedom that seems to come from startup but on the other, I used to be in the military and I appreciate structure. I'm also not sure I'm a great culture fit for many of the startups I see (both from a dev standpoint and from a personal one). Granted, I may not have a choice. I'm hoping to go into remote work due to health issues and I'm not sure how prevalent remote work is in the corporate realm.