RogerMurdock:
Alright. I went back to the drawing board. You're narrowed down now mostly to an Alaska Award. Still not seeing anything on 7/9, but....4 people on 7/8 from FRA to MSP again for 55k/person in Business class so enough to get the 4 of you to MSP. You will either have to buy 4 tickets from MSP to PDX (looks like Delta and Alaska will be the only options and it would be a horrible use of Alaska miles to book those). I would recommend using your Amex pay with points to cover that one. You will get control over the layover. Condor flight lands at 6:15 pm and theres a 10:10 Delta flight and a 7:55 Delta flight for 191$ and 223$ perspectively. Maybe you can get the other 2 to chip in on that one. If you're staying in Tuscany you should be able to fly from Florence to Frankfurt direct on the 7th when you depart. Let us know if you book.