Good for you for re-evaluating and for keeping things in perspective.

As for answering your question, it still might be good to get some info on your preferences if any and on where you've been before. My own advice for someone who's well-traveled would be different than for someone who hasn't been outside the country.

That being said, while the Maldives and French Polynesia properties are great, I don't think I'd recommend them for someone traveling alone. They're much more couples-oriented and the case of the Conrad Rangali somewhat family-oriented And in the Maldives, there's no place to go explore, since you're just on the Hilton hotels' islands themselves. If you're the kind of person who could nevertheless be comfortable just hanging out in a beautiful place by yourself, though, you might keep these places in mind.

As someone suggested, the Conrad Koh Samui that's opening this year might be great. Sounds like it will be a very nice property. It's not yet clear whether it's completely off on its own stretch of beach with no other hotels, restaurants, sights, etc. nearby, but even if that's the case you could rent a car or use taxis to bop around. More generally, Thailand is a great combination of being relatively inexpensive, efficient, hygienic, friendly and hospitable.

Also in Thailand, for a nice change of pace there are reportedly nice Starwood properties up north in Chiang Rai and Chiang Mai, with the former being a smaller city and the latter larger. I'd recommend a beach destination such as Koh Samui over going up north if you're only doing one or the other, though.

If you want more of an urban experience, Hong Kong is a fantastic city--really more a territory perhaps as big as Rhode Island, really, so there's lots to explore. Or you could combine a Thailand beach vacation with Hong Kong and/or Bangkok. I'd heartily endorse the Conrad Hong Kong.

Wherever you go, bear in mind that the climate of course plays a big role in the best times to go to specific destinations. Our USA winter is good for Thailand and Hong Kong, for example.

I also love London and Amsterdam, especially if you haven't done much or any travel outside the USA, as places to get your international feet wet. But I don't know much about the Hiltons there.

As for the challenge of getting enough miles to get to these places for free, check out the Miles Buzz forum. If the AA 75K miles and BA 100K miles deals are still open, for instance, you might consider applying for both of them--in fact, lots of folks (myself included) have had success getting two or even three of the AA cards.

I'm less clear on what the best UA/CO card deals are right now.