if I telnet two different servers at the same port from my pc, would one finish until the other one's done? does the outgoing port only allow one outgoing connection at a time?
They are separate and are distinguished by your local TCP port number, which is different for each outgoing connection.
http://www.tcpipguide.com/free/t%5FTCPIPClientEphemeralPortsandClientServerApplicatio.htm
servers respond to clients; they do not initiate contact with them. Thus, the client doesn't need to use a reserved port number. ... To know where to send the reply, the server must know the port number the client is using. This is supplied by the client as the Source Port in the request, and then used by the server as the destination port to send the reply. Client processes don't use well-known or registered ports. Instead, each client process is assigned a temporary port number for its use. This is commonly called an ephemeral port number.
There is a difference between the source and destination ports. The remote servers may be using the same port but they are different destinations host1:80 host2:80.
Each connection will use a different source address localhost:random_port.
A tcpdump or wireshark capture of the wire traffic will show the TCP network packets tagged with both the source and destination addresses and ports so that the network traffic has a return path.