I have been comfortable being useful doing remote work for a SV client for close to 4 years. But do worry a lot recently about ageism etc. So this page article and discussion is very useful for me.
In some months, I will try to share my experience of 'how it went'. It will take that much time, as I would devote 6 weeks at least for learning, and then try to go through 2-3 tech companies in parallel, as per the common advise I have seen.
As an employer I have been in a situation where we had 3 perfectly good candidates for s position, any of the 3 would have been fine at the job, but there's only one post. There was no reason for rejecting 2 of them other than there was only one post to fill.
While we didn't have discrimination issues to deal with there, it would be hard to show (if there had been) that we were being ageist or whatever.
I can completely see though that hiring someone at say 30 may be more attractive than hiring a 58 year old. I might feel that a 58 year old will retire soon (so I have to hire all over again), or that they might have a "don't tell me how to do it, I've been doing this for 30 years" attitude, which can be unhelpful. That's balanced against greater experience meaning they should be better at the actual job.
I can certainly see how over 55 makes you less attractive than compeditors for the spot.
Once they hire you, they're actually committed.
(Almost) All's fair in love and interviewing.
Dye your hair to your old natural hair color, nothing exotic.
Wear a bit of makeup to hide wrinkles and other artifacts of aging.