So I had a domain with Tumblr (who registers domains with Automattic and the email came from WordPress) and submitted the transfer out request in as you can see above, on the 8th of this month. It was supposed to be done by 3:41 this morning. It's now almost 5 pm and it's still not finished.
I reached out to Tumblr support the day I submitted the transfer out request and they JUST replied this morning around 1 AM with an answer that had nothing to do with what I asked. My question is what is my next recourse? The sites been down since the 8th, which is holding me back for getting everything back up and running at the new domain provider.

Why was your site down since the 8th? That has nothing to do with transferring a domain.