You might be able to. A $5 droplet on DO, configured correctly, should be able to handle a Hacker Newsering. =) The cache plugins for WP are really good these days.
DigitalOcean, it's not shared hosting and therefore harder to configure, that being said it's definitely worth it. I've found that even on a low-end VPS you can juice it for more than you could with a high-end shared hosting account.
You guys are talking about things that should be discovered during development, in which case, I'd rather have the exception thrown and showing in the console than to try to write a function to handle them.
Even in that case, it's easier to understand the exception if you have a meaningful stack trace. A good promise implementation gives you that.
Also, I guarantee you will always get exceptions in production that you didn't see in development. Browsers are different, users do things you didn't think to test. If you care about quality, you need a system in place for reporting those exceptions back to the mothership, again including meaningful traces.
Well, your degree seems mostly useless for your chosen line of work, so you don't really need the diploma, but as you already know and stated, that's stealing. It would also kill your credit score meaning that you might never have good enough credit to buy a house.
That depends. If I feel like I've accomplished all I need (or really wanted) to accomplish with the first startup and I'm excited to start another one, then there's no reason not to. Besides, you can probably make more money in the sale than you would need to get the next one off the ground.