We hit a milestone recently: 4000 files uploaded to Timestamps. It's been slow and steady over the last 2+ years of running — averaging 4 or so uploads per day since March 2020.
I continue to not do much maintenance work. I check on the site usage regularly with a small no-code app I built. The Timestamps backends logs to a google sheet, which acts as the database for an Appsheet no-code app for browsing the upload data and making some graphs.
There was legitimately one bug I fixed. I FL Studio 21 made some change to the way they emit .flp project files that was causing crashes for 1 user. It was a simple patch, but required me to set up the dev env for the first time in a while.
A unique experience that happened was I got in with the lead singer of Weezer of all people. Funnily enough, he commented on my original post in the Ableton subreddit saying he had a similar use case and was interested in this. Ultimately he had a separate solution and didn't use Timestamps, but it was still very cool to be in touch with him.
https://www.reddit.com/r/ableton/comments/fn4a3q/comment/iin63hm
My "enterprise customer" got back in touch recently just to check in. They still pay $10/mo to cover server costs but we haven't spoken in a very long time — maybe 2 years. That's not great on my part. I probably should have checked in more with them since then just to show that I'm still around and here for them.
Overall, things are still going well and I'm happy with where they are. A few uses per day and I'm still thrilled that anyone is using this at all.