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I'm sure there are reasons the implementation might not be easy, but conceptually this seems fixable. You just need a lower bound of "how bad can this plan be?" and that doesn't require completing the query, just observing that it's been running for a long time and/or used unreasonable amounts of resources.

Also, is the problem with the 50 join query that the planner screws it up, or that it's fundamentally doing too much?

You'd still need analyze to gather table statistics to have the planner produce plans prior to getting any feedback from the executor. So, before getting feedback, the quality of the plans needn't be worse than they are today.

> 50 JOINS

And no indexes.