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desktopapp

Nothing out of the ordinary. I've always looked at it as free advertising. Make sure they need to crack every version and make sure you can shut down a rogue serial number from your activation server.
Not too many average consumers willing to pay $50+ for software. But if you can find something with a reasonable sized market [developer tools] where people are willing to pay, then go for the larger base of users. But the days of average people buying novelty mac apps for meaningful money is over. The low hanging fruit is being given away by the OS or Google or some freemium offering.
1. Electron but obviously not a decade ago

2. All out. A couple contract jobs until ramen profitable.

3. Scratched own itch

4. Growth kept happening.

Surprised to see the random comment I made surface on this. Dug back out the anon account if anyone has questions or needs encouragement to strike out on their own.
99.9% of users have no idea they are inside a web frame. And so what if a good app uses 100-200M of ram these days? That's like one tab in Chrome. Electron has very low idle CPU usage, which I think impacts more users than does the memory. Each of those cross-platform widget toolkits look like shit.

The bigger issue is obviously lazy developers not polishing their electron app, but you can do basically anything with it.

I think it depends on your software and your price point. You're never going to sell a $20 app as SAAS without a service component. 1Password probably didn't have a long term path forward selling a stand-alone $65 password manager. Certainly something worth thinking about from the beginning. If you can have a desktop app that integrates with a service and have SAAS pricing you will be truly living the dream.
Exactly. Windows is a much much larger market in terms of number of devices and Mac is larger in terms of pros that pay for software.

And there is huge value in supporting both. If somebody wants to buy an organization-wide license, they almost certainly have lots of both and if you're being evaluated against a competitor that only supports one platform it is quite the leg up.

Tool. Comment answered next question. Distributed on own site.
People pay money for productivity software/tools. Look at how many tiny ISVs are making fairly large amounts of money selling Git clients. I think 1Password has like 60 employees now. There are companies much larger than 1 person doing screen capture software and large companies selling remote desktop solutions.
Good SEO, reputation, big market, staying alive long enough that word of mouth starts to mean something.
It's a full time job, with an extra helping of anxiety.
Most software sold as a license via a microISV has very little overhead/fixed costs. Whatever you sell you keep.

It's been a bit over a decade.

Running solo doing around $750k/year on a desktop app. The market is so huge and so many niches to filll. Make something you can sell for $50-300 with upgrades once in a while and set up a simple shop. It has never been easier to develop desktop software. If I was going to start this route today I'd 100% make an electron app and try to address and already large market that has stagnated or has shitty entrenched players making a ton of margin.