OpenHAB3 Start Up Issues - Race Condition? How to Sequence Startup?

Never assume. Search the open issues on openhab-core. See How to file an Issue.

But, as was mentioned and hinted at above, a ton of work has been put into startup. I wouldn’t expect an immediate solution to be implemented, if ever.

Frankly, the fact that you didn’t have problems in OH 2.4 was a fluke. OH 2 has way more startup problems in general than OH 3. So even if you don’t get immediate satisfaction on this realize that it’s not because the devs don’t care. It’s a really hard problem.