Absolutely; this is one of Tesla's key advantages, IMO, that they are building a huge database of charging and usage data because all of their cars and Superchargers are networked. Keep in mind that the Roadster went into production in 2008, and there are a fair number of owners who are over 50k, I think a few even above 80k on the original packs. It remains to be seen how their management system works in large volume though. It may be that they aren't being conservative enough, but that may be a cost they have to bear until technology allows them to increase energy density further to allow that larger buffer.
The way the battery in the Prius works is that it is constantly in use. Every time you let off the gas, or step on the brakes, it regenerates some of that energy back into the pack, and then uses it up again when you accelerate. Except for pure highway driving when you go hours without braking or even coasting, the pack is pretty much being constantly discharged and recharged.