So here is where I'm at, two primary choices.
A) Fly down to Seychelles from Israel, stay 4 or 5 nights at the
http://www3.hilton.com/en/hotels/seychelles/hilton-seychelles-northolme-resort-and-spa-SEZHIHI/index.html?WT.mc_id=EPEMHIResconfEN for 50k points - 20% per night. Since I'm Gold, I would receive breakfast (if they have kosher), and free internet.
-I put this room on hold as a purchase, and when my HH points transfer, I will hopefully be able to rebook it using them.
-Biz class tix from Israel are 90k, although I saw that Ethiopian airlines seems to charge around 1k for my 2 month old.
B) Fly to Maldives and stay at the Sheraton for 8k + 150 per night. The transfer fee is 100 pp and around 50 for the child. The room is a smaller room (500sqf vs 1,000), and I don't have many of the amenities.
-Biz class from Israel is 70k.
The 2 Hiltons in the Maldives are a more distant option, mainly b/c I would need to pay about 1k for the transfer fee. If I swallowed this fee, the Conrad had availability for 50k (40k after discount) but it's non-refundable, so its a risk. The other Hilton doesn't have any availability using 50k, but as stated a few posts ago, they have water rooms for as low as 365 (after tax). This seems like a good rate, especially since you can receive up to 15 HH points per dollar spent, and if I sign up for the HH card from AMEX or Citi, I would receive another 6 points per dollar. Additionally, they have a promotion going on now that could make the final take be in excess of 30 HH per dollar (around a 20% rebate). But again, the 1k fee is throwing me for a loop, as well as these hotels not being refundable once booked.
Regardless, I intend on stopping over for a day or so s/w in Europe, since Doha is a gateway city, and the flights to both Seychelles and MLE go through there.
Thoughts?