Originally Posted by MilesGator

To rack up Hilton pts/free nights you have numerous options:
1) Amex no fee Hilton Honors card
2) Amex Surpass Hilton Honors card (may be possible to get the no fee version first, then upgrade to the Surpass later thus enabling you to get bonus pts on both with only 1 hard pull)
3) Citi no fee Hilton Honors card
4) Bank of America Virgin Atlantic card (these miles transfer to Hilton 1:2)
5) Bank of America/Bank of Hawaii Hawaiian Airlines card (transfer to Hilton 1:2)...though I'm not 100% sure both/either of these cards are still available
6) Citi Hilton Honors Reserve comes with 2 free weekend nights (plus Gold status)

#'s 1-5 all offer different Hilton Honors pts sign up bonus (as compared to #6 which offers free nights).

You would have to do some research as to the specific sign up bonus's for each card to see how many potential Hilton pts you could rack up. Then you'd need to see how many nights you could get with that many points in the destinations that you want to go to. And also don't forget that during your business stays you will be earning even more Hilton pts to add to your balance from credit card sign up offers.