So, I got my 100,000 point sign up bonus a few days ago, then transferred 90,000 of them to United and booked two tickets to Hawaii for next year for $22.50. lol. Next, I booked the hotel stay and paid a $300 deposit this calendar year and the remaining balance on the hotel will be charged next year when I actually take the trip, so I'll get the additional $300 dollar credit then.
Two round-trip tickets from the DC area to Hawaii and a one week stay at a resort all for like $250 or so out of my pocket. lol. Thanks Chase!