Hi Brody,
Loosing restore points could be caused by low disk space.
If the free space on any partition system restore is monitoring falls
below 50MB, System Restore will SUSPEND & PURGE all restore points to
free up disk space.
I would suggest stopping System Restore form monitoring any
drives/partitions other than the one Windows is installed on.
Here are some troubleshooting tips for System Restore in Windows XP.
Go to Start - Run and type eventvwr.msc and press enter.
Click on System in the left pane.
Click the gray title "Source" at the top of the source name column in
the right pane to sort by source name, look for "sr" and "srservice".
Double click on each of these events, then click on the button below
the two arrows in the upper right corner. This will copy the event
information to the clipboard. Paste the information for each of the
two event here. This will help us in diagnosing the problem.
System Restore Failures to restore:
http://bertk.mvps.org/html/srfail.html