I think you bring both wing guys back, which is why if you're going to draft anyone to play on the perimeter it should be a 3. Shumpert and JR are going to be on the Cavs moving forward, I don't expect JR to get anything more than what Nick Young got on the market, he's going to be valuable to the team he's already on and nobody is going to take the chance on him.
I'd go big over small, you can always trade for Iguodala, and having someone like Upshaw is a good insurance policy in case Mozgov leaves or when Anderson takes his usual 60 game vacation. It's better to be overstocked with big men than to need one and not have one.
I'm positive that they re-sign Dellavedova, Thompson, Shumpert, Love, and Smith. I think they end up bringing Perkins back too.
They need a short and long term plan behind Kyrie. He needs his minutes scaled back going forward.
Which is why I think they need to draft one now and get Mo to sure up the back-up spot now.
Moz/Love/Tristan/Varejao are going to to take all of the minutes at the 4/5 spot. When he does return, Varejao's minutes will be dramatically reduced compared to what they were before.
When the Cavs go small they tend to do very well.
If someone like Upshaw falls far enough and they like him enough they could just buy a pick.