Human capital side would disagree with that I think. You're assuming the organization which owns this small/medium web app has the personnel already on staff to handle such a thing.
If you're outsourcing that, you'd likely have to pay a boatload just for someone to be available for help, let alone the actual tasks themselves. Like you said, if you're on-prem and something goes down, you can do something. But you've gotta have the personnel to actually do something.
That said, I think you're spot-on as long as you have the skillset already.
Depends entirely on the career you're looking to go into. There are certain fields that do, and should, require a college degree and appropriate certifications.
Assuming you are looking for a job in software development (since that's most of what HN is), the need for a college degree is becoming less and less. Some people are going the bootcamp route, some people are going self-taught. Just something to be aware of in terms of the talent pool, there's a ton of junior talent right now so it's hard to stand out. Actual projects you can showcase on Github and deployed on things like Heroku will be a good start
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