Well, I bit the bullet and booked our flights last night! Thank god, as I was literally checking prices multiple times a day and driving myself nuts.
We went with the Westjet/Delta combo: YHZ, via YYZ, MCO and then MCO, via BOS, YHZ
I was freaking about the tram, but the MCO flight is an actual Delta flight and the tram doesn't affect those gates! And, I like not having to worry about customs until we get home to Halifax...likely a long with thousands of others returning from down south all inclusives...doh!