Here's what I'd do:
1) 2 Citi AA cards each for 50K miles so 100K miles. Depending on which version you apply for you could also get 2 lounge passes and a $150 credit for any AA purchase. So buy $150 gift cards and get a statement credit to cover it for free.
2) I wouldn't waste a Citi application on the Hilton cards - at least not on your 1st churn. Consider the BOA Virgin Atlantic which offers 50K Virgin Atlantic miles (different from Virgin American) and can be transferred to 100K Hilton points.
3) Any Hilton AMEX card which will get you access to the discounted AXON awards so that Hawaii stay will cost you less points.
Good luck!