Looks cool, I think you should try to target it towards the elderly. My 99 year old grandpa is capable of using a computer and browsing the web, but struggles whenever he gets out of the "usual flow" (accidentally removes the chrome icon from his taskbar, whenever the crappy web-based email he insists on using over thunderbird moves the add attachment button). I end up having to do teamviewer to show him what I can't explain over the phone. He would very much use an assistant that shows him what to do, especially if he can speak to it.

Nicely conceived! This is the kind of feature Apple ought to have already delivered with on device models and private cloud compute.

Sending many whole screenshots to an indie mystery box, though, should be a non-starter for anyone without the skills to verify what any given update to this app is doing. Your website's featured use case highlights the risks (to you and users) unintentionally well: "How do I export my passwords?" (I did a double take: was this performance art from The Onion?) If a user opens a plain text file of secrets without closing this app/the help task, what gets captured, sent over the network, and saved to disk? What protections exist for, say, a computer-challenged elderly person's banking details?

A suggestion about the FAQ ...

"Where is my task history stored? Is it private? Your privacy is our top priority. Your task history is stored securely and encrypted on your local machine by default. You have full control over your data."

... This invites unanswered questions about what exactly from the screenshots is stored, for how long, and what design backs the "securely" claim. Being up front about this would invite trust and helpful developer feedback.

What data do you extract from interactions?

Checkout https://techcrunch.com/2016/05/02/google-acquires-synergyse-... ..

Google acquired these guys back in 2016 to help users learn how to use Google cloud products via interactive tutorials using a step by step guidance / walkthrough (the user had to install a chrome extension)

One of the best use cases would be edtech … think of interactive labs where your product can guide learners / students to complete a task and hand hold them ..