Billions of miles of travel by superchargers since 2013 show this strategy would be a huge waste of time, both for you and for the next person waiting for your space at a busy supercharger. If you don't want to leave when the nav says you can, fine, pick an estimated percentage on arrival that you are comfortable with and leave then. For example, if you don't want to leave when it estimates you will have 10% on arrival (31 miles), leave when it estimates 20% on arrival (62 miles). But waiting for your battery to go from 90% full (279 miles range) to 100% full (310 miles range) will take at least 20 minutes each time for those additional 31 miles.
The risk that superchargers aren't working is < .0001%. Probably a few more zeros. In six years we can probably count on two hands the number of times an entire site was down. It would require power to be out to the site, not just a problem with a supercharger cabinet, because the cabinets are independent of each other. I can think of Shamrock, TX during a storm, Huntsville, TX when a backhoe digging in the parking lot cut power, Harris Ranch for I don't remember what reason, maybe a few others. In six years! Then the risk would only occur if the outage happened while you were en route, because nav will not direct you to a supercharger site that is down. Even if the site has reduced service, meaning reduced power or some stalls out, the nav will tell you.
Bottom line is pick a margin of safety you're comfortable with, but there is no reason to wait for those last few electrons to move across the battery before you start moving to the next supercharger.