Now, this is quite a broad question (what skill to acquire, how to "sell" it and yourself, which companies to aim for, tips to retain sanity as a semi-hermit etc.), so feel free to answer whichever facet of it you find more interesting.
After that, it becomes much easier to get another remote job: you are already working remotely, which means you have a strong position from a negotiation standpoint when you ask for a remote job to future employers, and you have references showing that you can effectively work remotely.
I know several people who work remotely and they all followed this path.
As much as it pains people, irregardless is a real word [1] meaning regardless.
It's worth considering that remote work is likely to make it harder to find future jobs because remote work usually means less interaction with coworkers and outside vendors and customers. So it tends to curtail the growth of a person's professional social graph.
I get a lot of work from visiting for a few days and going out for drinks while I'm in town.
One time I got a high six figure contract that was going to go to a competitor the day after having beers with a few of the guys. I asked them to meet up so they could let me know what they liked and didn't like about my proposal. We talked about it for a bit but mostly just hung out.
The thing about remote work is that you still need to maintain the person-person interaction.
Know decisive people, managers, architects, entrepreneurs, also these who are far from your place - think global. From time to time ask them how their projects are going on, just let them know that you are available to help them. If they trust you they will come back after some time. There is always a shortage of good specialists so your pitch should be remembered.
Know your market - obtain skills which are remotely marketable. Just do some research what these people use, what stacks, what teamwork tools (Slack, Github, Stash, wikis, reviews etc) etc. Try to figure out their needs. Make a tailored CV every time to emphasize your skills and experience which match their needs.
Then you need some luck. As in every sale process that usually means repeating the process and constantly researching needs. Being on top with contacts and skills should help you close the deal, no mater where you are located.
From my experience it is easier to work for global or remote-first companies. Their main communication happens over distributed medium which is usually transparent for all remote peers. However if you are going to be just WFH guy in office-first environment then expect lack of information, dealing with poor communication tools and being forgotten when decisions are made.
I'm not saying it should be this way, but there are very many companies and industries where a long open source development history won't be seen as a reflection of what the developer can do in a job. Not all companies are going to take an interest in GitHub history.
I think the majority of development jobs are with companies that have a skepticism of their employees contributing to open source projects because they don't understand it and are worried about their IP being co-opted into open source.
The Github is overcrowded with mocked contributions just to boost resumes. I am not against open-source contributions and putting them on CV, but foremost they should be done not for fame but for community benefit.
Also I laugh when closed-source only company asks for GH contributions but they don't contribute anything and don't let one to work on GH in paid time. That means you spend your evenings and time off to keep up with GH - only if your contracts permits that too.
I worked in a closed, secretive space for a long time. When I left the secretive space, I had no public "street credit" that would've helped me land remote work. I had to rely on referrals. I'm 100% certain public code and street credit would have made my potential clients more comfortable with me. Plus, having the benefits of having a long, extended public track record communicating with others would have helped too.
A lot of companies where I’ve seen remote work allowed, only (explicitly) allow it for software engineering roles. And any other postings from the company will specify a particular office location.
I’ve been allowed to work remote in my current company, but only as a quirk of the org structure here and getting lumped in with the dev team. I do more of business operations and analytics work that usually doesn’t report up through engineering, and trying to find a new job that allows remote work has been painful.
I work remotely, but it is with an online writing service, plus as a blogger who gets a smidgeon of Patreon money and as someone who does resume work and advertises it myself. I don't have a remote "job" per se.
I worked for a time at Aflac. While I was there, they were trying out remote positions within the claims department (where I worked).
I am also trying to create a support system for digital workers, including but not limited to remote workers. This is the current page of remote job boards and what limited stuff I have for that area:
Some of that is related to the work (customer service especially) not requiring much collaboration with the in-office team, and long-time employees who moved out of town arranging to remain employed remotely. The rest is the fact that the business development folks are more effective if they're already located in and have networks in and a finger on the pulse of the specific geographic markets they're targeting.
That said, the business development job postings do specify markets where we expect the candidate to be located, just not the same one where our central office is located.
We also employ contractors in a few departments who work remotely.
I can't recall analytics jobs but try some of the normal sites and see what you can find.
Also this: https://github.com/lukasz-madon/awesome-remote-job
What does any of that have to do with being remote? And why is having to work at midnight a good thing?
Specifically you need to demonstrate you can work independently. This can be both job title ("senior software engineer" often maps to this) but it's also about a set of skills you want to demonstrate in your resume, cover letter, etc..
For long term contracts it is better to stick to constant daily rate, whatever you are on site or remote, as this makes companies planing and accounting easier. Of course it is fine to charge for travel expenses but that should be also agreed upfront.
Depending on work arrangement your costs may be even higher with remote gig - work space, utility bills, software licenses, hardware, occasional travelling, accountant etc.
You misunderstand. Remote is the normal salary you want. The on site salary is normal salary + 50% inconvenience fee.