They could put a drain on the filter, but that would be just as big a pain as changing the filter.
The dirty oil left in the filter is the only problem with keeping the old filter installed if you trust the filter is fine.
Is that amount significant? There is also dirty oil in the engine passages that doesn't come out.
With the savings on the filter, theoretically I could put the money into changing the oil a little more often so that the "dirty oil" isn't quite as dirty. And, besides, that "dirty oil" is the same dirty as it was before I changed the oil (at 100% dirty concentration); if it is so horrible, I should have changed it sooner.
I wonder which method is best for cost/benefit? I'm not going to try to think about it, but anybody else is welcome to consider it. It's probably close to a wash. If you have one of those cars where the filter is difficult to access, that may be where keeping the filter for 2 oil changes comes out ahead.