Hmm... could be a hardware problem, actually, with data not getting written properly. Do you have an SSD or an actual hard disk? If a magnetic disk, you might try running a good set of diagnostics on it. There are diagnostics for SSDs as well, though I'm not sure if the standard Windows disk check utilities are good for that purpose.
Alternatively, it could be software interference. Do you run any third-party security software (anti-virus or firewall)? Are there any error reports (in the Event Log, or possibly in the install or data folders of those programs)? Are you running the programs in Compatibility Mode?
Have you searched online for help with this issue, or contacted the vendors? XDA is a developer forum, not a support forum. You'd probably have better luck asking MS, for example, about the Streets and Trips issue. Alternatively, there may be support forums for those programs where other users have found, and fixed, the issue.
Also, Gateway is still around and making PCs?!? Whoa... it's like 1998 in here.