1. Not unfeasible I guess, but difficult due to licensing issues.
2. That'd be pretty cool and probably feasible to implement with a similar interface to free agency. Teams would of course be restricted to their D-League affiliate.
3. Definitely.

I'd also add that it should take place in "real time", so even though you might have to advance a day to make the trade official you could work it out without a series of PDA messages over a few days. And the Cancel/Confirm trade feature, so you can propose a couple of possibilities before going through with a deal.