Here's what I'm thinking
6 Hotel stays (10k+points at Hyatt will almost pay for itself)
6 Car rentals (will likely do anyway over that period of time)
3 Hotel Transfers (Hyatt, SPG, PC)
1 Get a debit card ($30, but includes 3k miles after first purchase)
1 Dividend Miles shopping mall (I'm sure something over that time will be eligible)
1 point.com transfer (10 PC, OR 2 Aero plane, OR 4 MR)
That's 18, now either I can gift someone miles, share miles (not really going to be worth it), emiles, e-reward, DM Dining (a lot of kosher restaurants), Thanks Again, or OfficeMax.com ($.25 paperclips or something)