Originally Posted by skw1

Hi, I'm a lil late to the points/miles game, but w/ a good bit travel coming up, trying to find the best strategy. I have both the CSP and CSR cards. Met both bonuses on a trip to Maui (flew Alaska Air) last month. Between sign up bonuses and regular spending, currently sitting on approx 185,00 UR points. Flying out of BOS, we have a trips/flights planned to GSP next month, NYC in April, Disney in October, and then Maui again in March of 2018. GSP and NYC flights are cheap enough to pay cash. Disney, I want to fly the family (2 adults, 1 child, and 1 infant) in business class (or like a Delta comfort+). Same for next Hawaii trip. So trying to see how to use the points for the October trip but save/earn enough more for the next Hawaii flights (BOS to SAN, stay overnight, SAN to OGG, then on the way back stay 4-5 nights in SAN.