9 out of 10 statups will fail. So if you're joining startups uou can expect them to (mostly) follow this pattern.

If you don't like this pattern the perhaps look for jobs at more stable (ie non VC) companies. And consider companies not directly in tech.

As regards to today, yes the job market is swamped. Don't quit your current job unless you gave something else to go to. But perhaps start actively looking.

Given you're a generalist, it's likely you'd make a good fit in a company which has been around a while, and which has a reasonable "IT" department, as distinct from a pure IT company.

re #3 - no, "jack of all trades" tends to be a career trap / dead end. companies hire for specific skill sets.

That only works so much. If a team goes from 3 people to 1 person, that's probably doable... you're leaving out a lot of communication. But from 6 to 1, you're going to have to prioritize what gets done and what doesn't.

But if you're working for the payoff from equity and the team size is shrinking that much, there's no payoff coming. Your salary had better be enough, but you should be looking for an exit.

If the startup is contracting, it sounds like the only potential upside has disappeared. I’ve been in a similar situation before and made the mistake of sticking around, to the detriment of my physical, mental and financial health. Obviously businesses pivot and turn around, but that’s the exception rather than the rule. Most startups fail, and if your startup is starting to falter, I’d say it’s about to prove the rule.

I’ll give you the advice I wish I had:

Run. Start interviewing like crazy and get another job. Good luck.