Preserve timestamps is greyed out. How can I change this? I am trying to use the "Keep remote directory up to date" but I keep receiving an error. I think it is because my timestamps are not UTC.
Quote from https://winscp.net/eng/docs/ui_transfer_custom#common:
The option is also disabled when configuring transfer settings for synchronization, as preserving timestamps is mandatory then.
Is this method the best method to use if I want to copy a csv file to the remote server whenever a new csv file is added to the local directory? I don't want to have to keep WinSCP open all of the time. If it has to stay open, maybe a scheduled task would be a better option?
Yes it is. You have to have WinSCD open for that obviously. But you can minimize it (even to tray). Scheduled task is another option, but obviously not as prompt.