In another thread @kennethlimcp is testing that recent patch. I have tried my best to help steer that testing - trying to explain to him what exactly UDP must behave like - but I cannot participate - I compile in the cloud. He seems to report better behaviour with UDP. Eveything has gone quiet recently.
Another user, @wlee, reports, same thread, 1.14 TCP is buggy.
@Dave, it seems to me that addressing your point (1) would make all the difference. The CC3000 blocks on difficulties connecting to the network. The Cloud is but a TCP socket. That can come and go, be closed and restarted, without blocking. Or ought to, and (1) would address that, as described by @Zach.