Dahl doesn't strike me as a business or product person. He's a genius when left to tinker. I get the impression Deno is floundering because of business/VC pressure. I see the original promise of Deno being compromised in an effort to increase users/customers. The project is no longer focused on just making a good JS runtime.
Deno's original positioning was as a second version of NodeJS without the learning cruft cluttering the environment. To that extent I think Dahl and his team was successful.
As is so often the case, once you introduce MBAs/VCs, the focus shifts to ROI and fast. I see Deno Deploy as being part of that attempt.
People still tend to forget that software development tools are not commercially viable. For a long time we have become spoilt for choice with ever more and improving tools.