If I understand you correctly, you just need a script that does:

https://winscp.net/eng/docs/scriptcommand_put#delete
https://winscp.net/eng/docs/guide_automation
https://winscp.net/eng/docs/guide_schedule

I'd probably have to do it in powershell if I wanted it to check every few minutes (essentially running 24/7 or whenever the computer is on) I assume? I'm still kinda new to scripting and completely new to WinSCP. I just recently switched over because of the automating capabilities. But say I wanted it to upload any *.png files in my C:\drawings folder to my server via sftp and then delete it locally after it's been fully uploaded. Or straight up moving it works too if that's possible.