As someone who does mostly custom videos..
Just in case members are wondering. "Checking up" before due date drives us absolutely nuts. If you have a question or theres something important, fine. But it feels like you're breathing down my neck. It became such a pain point for me I asked a sub of mine to create a custom tracker. Now i give customers a link and they can see where it is in the process. Recieved, Preproduction, shooting, post production, editing, delivery. Overall it's been well recieved. It's been interesting to see how often ppl check. Some, none at all. Others its close to 500 times.
One person recently kept messaging me anyway and when i gently reminded him about the tracking link he told me he messaged me as a "way to get to talk to me" which was silly since he was on a paid subscription page and free dming comes with that.
This past year I have adopted an "over communication" style with my customs. On top of the link, I email them the day of the shoot and let them know how it went, and restate editing timeframes. I also update when any items purchased arrive, etc etc. I communicate far more than I used to, and it has been a huge factor in terms of repeat business.