Hi tenor20,   Really appreciated as you are actively using SupportAssist and providing feedback to us. We have noted down this concern as new product enhancement and this will going to be delivery with new release of SupportAssist.
The settings page for SupportAssist is woefully short on options. SA reclaims space by getting rid of what the app deems to be useless programs (install files, etc.). But the idea behind the recycle bin is that you can restore a deleted file if at a later time you realize you shouldn't have deleted it. I don't want to go in there to discover it empty. If I want to delete something permanently I'll just shift delete and skip the recycle bin. I want to use SA, but this functionality has already burned me once and I'd like not to have it happen again. Any suggestions?
SA, configure to NOT empty the recycle bin?