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.
- 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 guess it can work if you work alone and with high autonomy.
For many jobs just having someone say "yeah fine" is not good enough for success.
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.
I'd always negotiated remote work upfront, but doing it this way is clever.
If you have no plan b, this tactic loses all of it's teeth.