I have also been struggling to get a tile package up to my online account.
I have a tpk which is ~50Mb. Yesterday I used the "Share Package" tool to upload it.
Left it running for ages, but noticed that the progressor bar would get to about 80%, then it would mysterious start again. No idea if it was doing different parts of the process or it was actually resetting itself. While this was happening my bandwidth was totally chewed up, so it was sending something somewhere.
Eventually cancelled it after 3hrs.
Any advice?
Cheers,
Neil