Sorry for the delayed response (no notification on mobile).
For some reason my relationship with the ceo was viewed as trusting whereas their programming team was not. I was able to get the time required (in 9 out of 10 situations) by explaining in detail why it was required.
We actually had a complete rewrite in the pipeline - an architecture written by myself - that was on the table. But they shut down before that was possible.
I don’t regret taking the position despite the frustration and difficult inherent to what I had to tackle. I got a very closeup view on technical debt that has assisted me throughout my entire career.