1X7 kept cleanish and oiled might get you further than you think, partly depends on how well distributed the wear is. Chains skip because the wear is mismatched, on a single speed where chain and sprocket wear together you can keep going till the teeth almost disappear. If you're predominantly in the same two or three gears, and a bit lucky, you might find it still works fine with those when the rest are skipping all over the place.
IMO, with a derailleur, you should either replace the chain before it wears the cassette, or run the lot until it misbehaves, I don't see the point of anything in between.