After some more testing I got my find session filtering working as desired after surmounting one additional challenge which I wanted to post here in case it helps anyone else:
It appears each session property set in "Extra Settings" can only have up to one corresponding filter on the find session side. In my case I had an int session property called skill, and I had two filters on it to make a range (one less than, and one greater than). Only one of those two filters was working. So I broke out that single session property into two called skill_floor and skill_ceiling (with the same value), and made a separate corresponding filter for each - now it seems to be working beautifully
Thanks again mordentral for your help here and making this incredible plugin!
It appears each session property set in "Extra Settings" can only have up to one corresponding filter on the find session side. In my case I had an int session property called skill, and I had two filters on it to make a range (one less than, and one greater than). Only one of those two filters was working. So I broke out that single session property into two called skill_floor and skill_ceiling (with the same value), and made a separate corresponding filter for each - now it seems to be working beautifully

Thanks again mordentral for your help here and making this incredible plugin!
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