Here is how to find a remote job.. find a remote FIRST company. Not a normal company you ask if you can work remote. Find a company that only hires remote people. Watching the companies that post on say weworkremotely.com and you will find something interesting.
That said, remote jobs do tend to have more competition. Since anyone can apply to any remote job, I suspect they get 20x the resumes of a local job (would love to hear for someone who has worked both sides of HR to confirm). So you can't just apply to 2 jobs and assume you will get 1 of them. It will take more work.
+1 for this. I worked remotely for a while for a company who I convinced it would be a good idea. It didn't work out well because I was the only remote employee and their culture and processes just weren't set up for it. I spent more time reminding people to dial me into meetings and convincing my bosses that I was actually working than doing my real job. If the company isn't already bought into having remote workers, being the pioneer is painful.
Our ad for a sysadmin got 100+ resumes, of which about 50 were trashable, and we had a dozen plus excellent candidates.
* Find a company that already relies on digital communication. Maybe they have a couple different offices, and employees communicate heavily over Slack. A company is unlikely to make this kind of change just for you, and I find it critical to working remotely with a team.
* Work for a number of years at a company and do a good job. Become a person they want to retain.
* Be an excellent communicator. Don't be the guy/gal who's hard to get ahold of because you're never logged into Slack, or because you check your email only once a day, or because you never answer your phone.
* Be upstanding, honest, and forthright. Be self-supervising. Be the person your manager doesn't have to think about, while still knowing you'll do an awesome job. Give them nothing to fear regarding whether you'll continue to do a great job without supervision.
* Be slightly underpaid for your market.
That last one probably isn't something to seek out, necessarily. But it's a good bit of leverage to use when trying to convince your manager that you should be allowed to work remotely. If you can convince them that letting you work remotely is free for them but a perk for you that's likely to keep you at the company, you've won.
Those few were very good at what they did for years consistently and well liked (responsible, pleasant, mature).
I consider whatever extra steps required (being nearly always available on IM, etc) for remote work is well worth it, because remote work offers so much benefits.
I used to think server/sysadmin was one job where you had to be there and that remote job was only for devs. But now with AWS and cloud computing, sysadmin for remote working is just as easy. Amazing how things change.
We used to do this via remote serial console 20+ years ago, then we moved to IPKVM, and now ipvkm over integrated IPMI controllers.
I've managed groups of sysadmins over the years, and the truly talented will outright refuse non-remote work. Since they can demand it.
Sysadmin/Devops here. To confirm your point, I don't take any work that isn't fully remote, and I don't take any position for less than $100k/year USD (~15 years experience).
Maybe I just haven't been blessed with working with crack team of sysadmins or a shop big enough to justify such investment.
Oh, and I used to work with Windows servers...