I also regret building some things in C# or Java a long time ago.
The biggest regret money wise is I built a crypto forecasting company that became somewhat profitable BitBank.nz but I built it without enough foresight for cloud costs, was running a forecaster constantly on compute engine as well as filling up a postgres database without offlining data, turned out harder to scale down a database than scale up the memory. Basically things like that and I never had time for it after having kids meant it long term costed more than it made even with paying customers so I shut it down.
Now I run https://text-generator.io still machine learning related but I run it very lean from two GPUs I own at home which is a bit easier