The start of my ladder looks much the same as yours except I jump from local files straight to single database SSR/SPA. Maybe slightly more complicated than a local app because you need auth, but when prototyping something I just use basic auth to start.

Chuck it up on a $5 DO box and you instantly get:

- Multidevice access, desktop and mobile (write mobile-first css and the tiny screens aren’t a problem)

- a UI that’s trivial to hack on (HTML and css are easy)

- likewise, a technical base that’s easy to extend. Drop in react, build out the api side and use it as a source for other projects, etc

All this assuming you have reasonably reliable network access, and even then you can build it as a clever PWA falling back to local storage if you need to (I think, prototyping that is still on my todo list)

Heck, save yourself $5/month and stick it on a raspberry pi at home.

It’s truly a golden sweet-spot for personal software tools. The only external dependency that irks me is needing a domain name.

All of the constituent parts are easy. It's when you tie it all together that it starts to get complex. There is no doubt there are many more moving parts in a modern web app compared to desktop. I did a few VB projects and I needed know two things, VB6 and a database.

Of course we can't go back, enterprises are rightly presenting their systems directly to the customer, you can't do that with a desktop app. None the less it does feel more complex than it needs to be.

Desktop apps are relatively simple if you only need to target one platform. Both windows and macOS have good options accessible from managed languages. But if you want to do cross platform then the complexity rockets.