I miss the days of VHS and DVD shelfs in homes, for example. If you bought the tapes and had them in your home, no corporate entity could alter those tapes without your consent, monitor how many times you watch them, sell your data to whomever they please without your knowledge, roll out new mandatory conditions to a 'user agreement,' or remove them from your library if/when they like.
I noticed some dumb change in how Dictionary definitions are shown in the Spotlight (ie, overall search my computer function) in MacOS this week. I've turned off all auto-updates, and I didn't make that change or consent to it. But despite paying the full price all by myself for this machine, I clearly don't have 100% control over it. It seems very clearly to me that consumers having control and privacy over their Internet-connected devices is a bygone era.
After Blizzard, the video game company, replaced copies of Warcraft 3 that I and others had paid for in full and installed on our computers that we could play without connecting to the Internet with a lower-quality copy that prohibited offline play - I swore I'd never pay for a video game again*, and 3 years later I haven't backslid on that. I felt so angry, cheated, and robbed by that. (*Edit: my criticism and frustration is really more with larger developers/companies/creators - I appreciate and am happy to support smaller, more independent and libre ones.)
Many people probably won't be bothered by these things, but I am. I don't want to pay full price for something that I don't truly own. I miss the familiarity. I miss the reliability. I miss feeling like it's mine. Dependable. Trustworthy.
Picking my old guitar up again has never looked so appealing. I think I want to go back to investing more time, money, and energy into things that aren't connected to the internet
Indeed which is why I was honest saying "it was hard requiring a lot of effort but, step by step, I removed a lot (not all!) of those terrible behaviors from my life."
Namely I don't even aim for perfection, just pragmatism. I have to use Windows at work (sometimes) and I hate it. Still, I do my very best to compartmentalize, namely I do not install such work related tools on my personal or even professional computers or phones.
In your specific case I would argue that have the free email from Microsoft but not using it for anything else and deleting it as soon as it's not absolutely needed is an acceptable compromise. I would also do my best to understand what "leaks" via this email or how you use it. Anyway my overall point being to be pragmatic because perfection leads to inaction.