I think the way to get a remote job is to start with a non-remote job and slowly convert it to remote. Haven't pulled it off successfully yet but it seems like a much easier path, so long as you're willing to put in the time.
My biggest "issue" with remote working is always when there are differing amounts of remote work within teams.
When you have half the engineers in office, and half remote, the 2 sides end up with communication issues. In-office meetings where a few are remoted in are awful unless the company spends the money on a real remote-conference setup, having co-workers that don't like to pick up the phone and call the remote guy ends up keeping remote workers away from the problems.
I will never work at a remote company that isn't actively working on maintaining a remote workforce. Because even though I absolutely love remote work, it's not easy, even for those that are heavily invested in it.
I lead a dev remote team and I have to actively communicate with people on the office to know about things going on. There is a shitstorm happening and we don't know about it until they need something from us.
I've done it a few times. This works better since you get a lot of the relationships, culture and company knowledge established before you spend less time in the office and if you do it slowly you all learn and fix what needs to be put in place to make it work well.
It doesn't work in all companies, but you can often work this out in advance. A good sign is obviously if some people already work remotely, but I have found where this works best is if the company already has teams spanning multiple locations and time zones and have the management structure and communication tools developed to do that properly.
