process connect (aka gdb-remote) isn't the clearest in its error messaging. We have everything we need to distinguish between three common failure modes: Nothing is listening to the port (or we could not reach the port), the remote side did not respond to the initial handshake packet quickly enough, or the remote connection accepts the connection and then drops it immediately (e.g. a debugserver might reject the connection because it is only accepting connections from certain hosts).
With this patch, we get
(lldb) gdb-remote 7000 error: Failed to connect port (lldb) gdb-remote 4000 error: failed to get reply to handshake packet within timeout of 6.0 seconds (lldb) gdb-remote work-imacpro:4000 error: Connection shut down by remote side while waiting for reply to initial handshake packet
and I think it's a little easier to understand the nature of the problem. Just fixing a little thing that's bugged me for a while.