I haven't had to worry about this in years but while working in retail I periodically found myself at a GP and being prescribed antibiotics when I would have otherwise stayed home to rest, if I didn't need that medical certificate.
I suspect that'll be a common theme in answers here though: if you have a side project making $2k a month, in most of the world that's enough for you to go full-time and try to take it further. If you can make $2k/month on something working only part-time, you can definitely make a lot more if you focus on it.
On your questions: HTTP Toolkit is a desktop app (plus a mobile app and other components for integrations) but it's an Electron app that effectively functions as a SaaS (with a freemium subscription model) that just happens to have a component that runs on your computer. And actually getting to $2k wasn't overnight at all - it took a couple of years of slow steady slog. A few inflection points that made a notable difference (releasing rewriting support & Android support particularly) but mostly it was a matter of "just keep pushing", trusting the trajectory would keep going, and steadily grinding upwards. It's great where it is now, but it's hard work - a solo business is not for the faint of heart!
Current income at 80k/year with relatively low maintenance. I have a full time job as a software engineer on the side.
Which has seen enormous positive feedback - and youtube ads are very fair (50/50 split between you and Google), and you don't have to chase the money, it's all handled for you! Another 10% of my monthly income comes from YT, I'd guess.
The key with a youtube channel is to differentiate yourself from the rest in some way. I'm trying to do that with careful script writing and high-quality audio. Don't just dive in and waffle for 30 minutes while screenrecording, practice!
But I've absolutely never seen it in the wild.
Contacting general or merchant support often took over 2 weeks to get a response, which was a deal-breaker for any service that would inevitably impact customers on our end.