It should not be difficult to create, say Perl/Python/PHP script, that takes you list of hosts and transforms it to WinSCP script.

I am looking to upload a single file to multiple servers. The list would change depending on which clients were needing the upgrades. Would like to use a text or csv file with each ftp ip, username and password per row. The script would grab the entry -> connect -> upload one file -> disconnect when completed -> move onto next entry.

I am not that versed in writing code :(, but when you have close to 100 sites to upgrade regularly, I thought WinSCP would be a great alternative to doing it manually.