Did seven days of cycling, the first and last days as DIYs from home to the CTC birthday rides. Stopped and reset the 500 at the end of each ride, then went back into it to check the last ride was in the activities log, which it was. After getting home, I uploaded to the home computer and only the last two rides uploaded. Turned on the 500, looked at the activities, and only the last two were showing. Looked to see if the five missing rides were hiding inside other files. Nope. Luckily, I used my etrex 30 each day, and all the rides were in the archive.
Only had problems losing files since upgrading to Windows 10 then reverting back when neither garmin would download routes for DIYs/events.
Could it be that the memory will only store so many rides now, I didn't press the option to delete old activities at any point. May buy a garmin 200/210 which logs rides.