Self-Esteem while Underemployed at 35? Is it Possible?

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Feel free to move to Coping with Life if so inspired given the off-work ramblings at times.

So I'm sick with a cold but working from home 11-7 save Wednesdays 8-4 (unpaid half hour lunch and $17.45/hr so less than my old job laid off last summer but insurance is cheaper so I squeaked it even basically), but have my mornings free all week since I can stay in if sick. Gives me a chance to take stock, take a pause, play the "sick role" as sociologists call it and be cared for without the stigma of the disability itself for a bit.

It's got me thinking about how I basically lost my promise. I grew up middle-class but didn't have the executive function to plan grad school or internships or take part-time jobs in school, plus my dad who divorced at puberty pulling the plug and my forced-to-retire mom's inability to get back in the workplace lost us equity and shifted me into rentals and created needless stress in my life. In the end, no matter how well I did in classes, I was a paper poindexter with no plan, and my B.A. got me essentially high-school jobs. I was lucky enough to get a call center job (for telecom) two years later instead of burger-flipping/retail etc., especially since I'm physically clumsy not to the point of breaking stuff often but to the point of mild dypsraxia and would likely flub any cleaning/food/factory/retail role I took on, and I was rewarded with a boost above the poverty line but barely as the wages went from $8.50 to $15 in a few years' span, but I couldn't handle 40 hours a week until I worked from home. I got a half year of building my savings while the call center closed up shop in town, until the contractor ended work from home and I was given an ultimatum to work in a smaller town with few industries, which only belatedly got me recognition for a full-fledged layoff but was not disputed for the unemployment that all my co-workers took.

After a year and a half of off-and-on job searches obviously intensifying once my old job went up in smoke, the only offer to bite was a mix of inbound and outbound calls/messages/packets for a company that processes HR claims for Leave of Absence, interesting work but with some clunky old software we've been promised a refresh of in July and baffling cognitive dissonance to contend with mostly from employer policy/messaging shenanigans I have to smooth over with employees. So once again I'm the middleman/clean-up crew, some nice co-workers but now I've gone from a one-and-done take-the-call-and-that's-it day-to-day to a workload process and negotiation demands that severely tax my abilities and leave my deficits embarrassingly clear; I'm still handling things at half the pace but being given mulligans on it and am not sure if those will end, to which point I've had to enlist vocational rehab as a potential backup which I never had to at my old job. I'm building savings again, but it will slow when the housing assistance my mother on Social Security (the only reason I'm not dirt-poor to be honest is living with her) got during my dry spell on unemployment runs out, and I'll probably only be able to save $100/mo with current cost of living if I'm lucky unless rent independently goes down. The biggest fear that I have , truth be told, is not getting another job if I can't hack this one and having to "prove" the severity of my disability and perhaps even injure myself or others taking more menial jobs to qualify for SSDI.

I'm discouraged because I feel like I don't have a "real job," especially for someone of my educational level and age, and feel like I'm too strapped for cash, clueless about my potential, and jealous of my free time for hobbies that may or may not pan out to writing or photography work to seek more training. The ship went off course, I fear, and possible Long COVID may be dragging me into brain fog and making everyday pain complaints I've had since I was way too young for them a bit worse (to the point where I changed my chair thinking work from home in a wire mesh prison might have been a factor too), though going off a med cocktail that kept me unmotivated but content until I turned 29 and saw the clock might also have blunted sedation masking. I've made some good friends through sociopolitical activism (lefty, sorry for those offended) and informal Meetup groups that turned into a trivia team still going strong after 5+ years, and despite everything social progress is very real and everyone from state legislators to regular Joe friends just 5-10-years older or 5 yrs younger (still working on those age peers like so many here). But boy, those women I meet on dating sites as opposed to off them, they see right through to the crux of the matter and I'm still a stunted kid in their eyes (5 foot 6 in the tall Germanic/black Midwest with a patchy beard at best I should probably save and clumsy doesn't help), good for a bit of fun and even a fling now and then but never "boyfriend" material and having to work way harder to attract because even the independent can size me up, and even putting aside the "man living at home" stigma that is dying excruciatingly slow in America, I can neither be provider nor backup. Those I move furthest with tend to be A-type women in service or healing jobs, maybe a bit of mental illness or ADHD etc., who like the groundedness but ultimately need more financial stability than I can offer to go with my emotional even keel.

I guess I'm wondering, even if I could cure Long COVID or whatever and get some burst of the energy I've been seeking to shoulder the load and change my life, what's my reason? I like existing and don't want to stop, but for building a life, what's my "how" and what's my "why" beyond not disappointing my mother? How do I avoid feeling eternally burned out and out of reach of anything resembling a normal life? With today's housing bubble, how do I make the leap somewhere more cosmopolitan without the job guarantee and with no experience living with roommates, or find the hard-to-sleuth corners I might enjoy more where I'm at hours from the nearest metropolis? What does a 35-year-old man invisibly held back do with the rest of his life? If it helps, I think I'll have somewhere around 10-12K in savings when expected expenses and expiring benefits intersect to keep my savings more or less frozen at some point later in the year or early in the next unless I get a raise, hopefully without having to plan for the immolation of democracy and the environment across the globe.

TL;DR: stuck at entry-level because I can't handle jobs enough to rise up the ranks and dealing with health challenges that may be more than just ASD, 35 with time a-wastin' and no wife I met young or friends from high school or college in tow to smooth the way, how do I launch late?

I think you need to get over your age fixation.
You aren't a female with a ticking biological clock!

Times have changed. Folks no longer stay in one job.
I know someone who left a very good job in Newspapers twenty years ago because he saw what the Internet was going to do to his job. He found another career before retiring.
Folks move jobs even faster these days.

Self-worth should not be tied to one's net worth - the Two are not related.

You could re-frame "under-employed" to employed. So many people on and off of the ASD spectrum are not right now.

People on the spectrum specifically are more likely to be unemployed or underemployed, not only versus non-autistic folk, but also versus disabled folk in general. I have seen the research in the UK to back this up, and I imagine it will be a similar situation in the US.

You are not alone in this situation, if that is any comfort?

Nobody has experience of living with room mates until they do it. I share-housed for 5 years (living with goths). It was good. I took over handling the bills for the house. It was actually a good situation. The rent was only a fraction of what it costs to live alone.
We each had our own room, and shared common areas (Kitchen, bathroom, etc.).
The main considerations relate to honesty (don't live with people who want to intrude on your space and take your possessions), and people who like too many loud parties are best avoided.

But if you can find a good spot, and if you can live out of one room, it could be worth considering.