So yes they'd be paying me and the server. However the server fees would be cents a month. I would aim to present this as a strength to the user: you get billed direct by AWS/Azure because you're not at ransom to me - you hold the keys to the kingdom.
I suspect you're right though: Technical people will DIY, and nontechnical won't care, and will simply use Wordpress (it's the IBM of blogging: "nobody got fired for buying Wordpress")
Indeed.
At some point the desktop app will need updates too. If the developer stops updating it it will be as good as dead.
Exactly. Windows and Android apps last forever. Not so much in Apple land.
It's not only that though. For example, something could be deprecated in the AWS SDK. If the app has to deploy somewhere it will be coupled to that too.
Or is the idea that the tool registers an account to a server provider for the user? So the user has to pay both you (for the tool) and the server provider (for the server).
Maybe I have misunderstood the aim? In any case, due to what you mentioned, I think it's a difficult niche, since technical people can set up their own and I'd guess most non-technical people don't really care enough.