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If I could make one recommendation: hire a UX/UI designer ASAP. The less technical the audience, the more intuitive and easy to navigate the UI needs to be.
Our company focuses on home service businesses and they get roadblocked super easily. I think you'll be glad you did it earlier rather than later. Otherwise, the ux debt will pile up and it will be quite a project a year down the line.
It's not that trades are super complicated in comparison to other fields like web development, it's that there's no GitHub, no source shared among all pros like "here's what I did and how I got it to work." Without a good stack overflow how does the AI judge the quality of workmanship in photos?
You are absolutely right, btw, about google drives and one drives and hundreds of photos and all that. My experience is in dealing with general contractors on smaller jobs, not supers on mega projects, but they have similar issues. Lots of sloppy back and forths and poor tracking of change orders, etc,
What Im trying to say, since I sort of rambled there, is that while processing and sorting and making punchlists is a good idea, I have doubts about AI's current ability to accurately spot code(as in building code, which unlike JavaScript varies by zip code) issues. Does the AI know that you dont have enough clearance at X or does that have to go into the recording?