I was looking at the wrong Chase Ink card. I've now signed up for the Chase Ink Cash card last night and am awaiting a response. If I go the Hilton route for the hotel points, when would be a good time to apply? Is Aspire the way to go?
Honestly that depends.
If you are able to max the benefits as far as the $250 airline credit and the $250 resort credit, then the Aspire card essentially pays for itself. The Diamond status and FN cert become icing on the cake.
Depending on how long you are planning your stay, you can probably accumulate enough points to cover the nights between you and P2. Standard room rates at the Conrad Rangali are running 120k per night but you literally need to stalk day by day if you aren't flexible in order to snag one. This means practicing with the site to try and figure out when award room availability drops. Each of the resorts has different windows for booking. Right now the Conrad Rangali is booking out until March 16th of next year and there is no standard award availability. I saw some standard availability (no OWB though) for December but none for Jan-March. Waldorf Astoria Maldives Ithaafushi looks like its booking out until the end of February and no standard rooms are showing. Hilton Maldives Amingiri Resort & Spa is booking out until the end of February and has standard award availability for Beach villas with a plunge pool. SAii Lagoon Maldives is booking out until March 16th as well with standard award availability.
Waldorf Astoria Maldives Ithaafushi standard rates are 150k a night. Hilton Maldives Amingiri Resort & Spa is at 110k a night. Only the Conrad Rangali has OWB for standard pricing from time to time. SAii Lagoon Maldives, Curio Collection by Hilton is 85k points per night.
The Hilton business card is at 165k with a $5k MSR
Hilton Honors card is at 100K with $2k MSR
Hilton Surpass is 150k with a $3k MSR
Hilton Aspire is 150k with a $4k MSR
In 2 player mode you'd have 850k Hilton points between the SUBs and MSR without even going for the Aspire and that would cover 5-10 nights depending on the hotel you choose. Points should be in place once your spend is made and the statement closes. Its the FN certs that take forever.
Keep in mind food is expensive in the Maldives and having Diamond status was helpful since we got free breakfast and cocktail hour snacks. Also the resort credit helped with the sea plane transfer which I'm sure has gone up in price. So those are things to consider.