I read Martin's reply above and read the two links, but as I'm unfamiliar working the commandline for WinSCP, I wanted to ask for some guidance.
Based on what I read from the two links provided:
1) For all sites, all my passwords are the same and I have them saved. Would this be the command I use to update my saved password to "mypassword" for all sites in a folder called "primary"?
winscp.exe /batchsettings primary/* PasswordPlain=mypassword
2) Where/how do I run this command? It doesn't sound right to run this from Windows command prompt because I would have to login into WinSCP first right?
3) If I want to change it for all sites, would I replace "primary/*" in the above command with just "*"?
4) I read that WinSCP will replace the option "PasswordPlain" with option "Password" on first start up. Is that guaranteed? Is there a way I can use the above command with option "Password" instead of "PasswordPlain"? If so how can I do this?