Questions I have about this whole transfer of accounts:

1. Currently a Surpass cardholder since May 2017. If I want to upgrade to the Aspire instead of the Ascend can I do so on 1/18/18 or do I have to wait until my one year Surpass anniversary in May 2018? If I can upgrade this month (mid Jan) when would the $450 AF hit?
2. Planning on staying at Grand Wailea this summer (5 nights all reward /no cash stay) so would we be able to charge things like food/restaurant, bar drinks, parking, etc to our room and pay for all of that with the Aspire card and that charge count toward the resort credit reimbursement? Also can the resort credit be used towards booking cash stays at the included resorts?
3. For the $100 resort credit could that be awarded for an all points stay at one of the included resorts or does it only apply to cash reservations (min 2 nights)?
4. if I stay with the ascend or upgrade to the aspire, would my anniversary now be Jan or would it stay in May?

Sorry for all of the questions, just trying to decide in my situation if it would be worth wile to upgrade or stick with the ascend. Husband and I both got the Surpass last May with the 100,000 bonus pts and free weekend night on 1 yr anniversary in hopes of using all of those benefits for trips this year, just trying to get a new game plan for both accounts now!