I 55 and have worked remote many times during my career (including currently). The best way I've found is to work onsite initially and dazzle them. Then when the contract is up tell them you are willing to continue remote.
I have done this so many times that now, it's my default routine. "Dazzling" includes not only the work that I do for them, but also by doing it as if I were already remote. Writing emails, requirements, specs, and reports becomes as important as writing code...
- impeccably written emails detailing everything about every project and keeping everyone in the loop
- documenting every issue, question, and plan of action via email, letting nothing fall through the cracks
- status reports like clockwork
- precision on requirements and specs, spelling everything out, leaving nothing to chance
- a great attitude and team player (barf barf) in writing
Do these things and insist that others do (along with all you other dazzling work) and they'll have no excuses not to keep you when you decide to go remote. They'll already know you're a "professional".
I agree this way is difficult to help you catch truly remote-first job, as requirement of sitting butt in an office contradicts it.
I recommend screening company with Glassdoor (WFH hints etc.) and at interview asking about communication/collaboration tools in use, remote teams etc.
Nowadays there is a large middle ground of companies which have globaly distributed offices. They may ask you to show up for some initial period to gain trust and mix into culture - definitely important for a long-term cooperation. Afterwards switching to remote is like relocating to different office but staying in the same project, which is pretty common practice. Tested myself several times.
The key insight is to have a better alternative if they say no. You have to be in the position to speak authoritatively about your subject matter to the extent that your client realizes your time is too valuable for tire kickers. Make the case that your best work is done on your terms. It's not that you don't want to negotiate it, there is simply no mechanism for you to provide the advertised services in suboptimal working conditions.
If you have no plan b, this tactic loses all of it's teeth.
- impeccably written emails detailing everything about every project and keeping everyone in the loop
- documenting every issue, question, and plan of action via email, letting nothing fall through the cracks
- status reports like clockwork
- precision on requirements and specs, spelling everything out, leaving nothing to chance
- a great attitude and team player (barf barf) in writing
Do these things and insist that others do (along with all you other dazzling work) and they'll have no excuses not to keep you when you decide to go remote. They'll already know you're a "professional".