Getting everything to work reliably. This was my first time handling a software with so many moving parts. If I could get the search query to work, I would break the date range filter, if that worked, the document indexing flow would stutter, or I’d discover a new bug caused by an edge-case.

Since I built this application in an exploratory manner (branching out without a larger architectural design), it often became unwieldy for a solo hobbyist like myself.

Plus, I wasn’t able to really get going with user feedback. Reached out to family, friends and colleagues but faced the Windows roadblock and got demotivated. In the end, built it for myself and used it by myself. I am happy with that!