Thanks for the helpful replies. I finally have it all figured out!
1. For Winterland, I did a little digging and found a thread where a Disney CM says that if we're still playing mini-golf after BB closes, we can just tell the CM on duty when we're ready to leave and the CM will call for a bus to come and pick us up. Sounds easy enough!
2. For Boma, I think we'll try waiting for an AK bus at CSR from 4:30-5. If one doesn't show up, it should be pretty easy to get a cab to take us to AKL.
3.
bigmac5, I think this is what we're going to do, too!

I had misunderstood a previous post of yours and thought that you were saying to take a boat over to MK for Wishes, but your latest post cleared things up for me.

I think we're going to take a bus from CSR to MK, and then decide whether to catch a boat or the monorail over to Ohana, depending on how much time we have. To get back to CSR after Wishes, we'll take a bus to DHS and then a bus to CSR. We can always change our minds and get a cab if we're super tired. (We will have been up since 4 AM catching our early flight to MCO.

)
4. joelkfla-- Thanks for the info on using the PI bus stop at DTD.

Man, how did I ever plan trips before the DIS??