Those are helpful options to take into account, thank you very much. Aeroplan didn't have any direct flights (1 stopover on the way there and 2 stopovers on the way home), which I guess I'd consider since the business class is cheaper than Delta coach. ANA had no Rome flights, but did have Florence at 68K business class. Although it says it takes 5-7 days to transfer ANA points - too much of a risk for me.

I'm going to keep checking ANA, AC and Delta regularly. It seems flexibility and creativity is key. Thanks again for providing some cost-effective options.

-Bocconi