For those that did this, how did you approach the conversation to the manager and what position were you at the company?
I attempted to transition into a remote position with a company when we made a move to be closer to family. I basically said, "I'm leaving as of the end of this month (a few months out). I'd like to continue working with you guys, remotely, but I understand that may not be possible." My manager supported it, and ran it up the chain, who supported it, up to the relevant C level exec, who said, "No, we don't do that, we find it doesn't work out well." Which... whatever. Their loss.
So I do remote work for other people instead.
The biggest thing is having a separate, isolated space dedicated to work. I built a shed on a corner of our property that I work from, and it's the best workspace I've had, ever. No distractions, and I focus on the type of work (typically fairly low level, detailed stuff that requires long form focus) I'm good at out there. Part time. The people I've been working with recently seem to remain confused that I do high quality, full-time grade output, working part time and remote. I keep struggling to explain that it's not that I do that despite being remote, it's because I'm remote - because there are no distractions, and I don't get dragged into random meetings. I task switch on a "days or weeks" granularity - I'll work on some project for a week or two, straight, then switch to something else, so I'm not paying context switch overheads.