expirobo:
Hello, I have been working all day trying to figure something out.
[...]
All in the same loop. Is there a way to do this this library? I'm dumbfounded.
First, you should go for EtherCard, the other libraries are not supported any more.
Second, while there isn't a lot of information on the libraries, my understanding is that each loop() can only handle max one packet. This means you should put your logic in some kind of state machine, and wait for the TCP ack from your first packet before you send the second one.
But I don't really master the stack either, and while EtherCard is "smarter" in its memory usage (almost everything in Flash and in the ENC chip), it's not reaaly easy to work with.