@Paco_NYC,

Are you able to access the router's WebUI through a wired connection? You may look to check to see if any errors are being thrown, or if remote control was disabled for some reason. 

It almost sounds as if your router is not properly contacting the TP-Link cloud servers. I would recommend starting with changing the DNS server for your network to a common service to see if there is a routing issue outside of your network causing problems. Similar cases have prevented users from being able to complete a firmware update, despite the rest of their network and connections working great.