What kinds of things do you like to do? Are you looking for a place where you can just chill out for two months or are you wanting a little more adventure?
Accommodations in Hong Kong can be a bit expensive (I mention this since you mentioned your apartment in Manhattan) and, due to its size, Hong Kong doesn't have as much to see and do as other countries in the region. It's good for shopping, however, and has an interesting vibe.
Many people absolutely love Thailand. Bangkok has a few cool things to see, but I'd really try to check out the islands down south (avoid Phuket and Pattaya, in my opinion) and then northern Thailand (as well as Luang Prabang, Laos, and Myanmar/Burma if you have time) instead of just spending all my time in Bangkok. Accommodations in Thailand are quite reasonable and it shouldn't cost you too much to get from place to place.
Backpacking through India would be an awesome way to spend a couple of months, in my opinion. It wouldn't be the easiest trip, but you'd get to see a lot of things--and it'd be probably change the way you look at the world.
I personally love Japan and think the Osaka/Kyoto area would also be a great place to spend a couple of months. It would be less of an adventure trip and more of an opportunity to see temples, etc., and enjoy Japanese culture.
Let me know if you want me to elaborate on any of this. I didn't want to go into too much detail about somewhere or something that you might not be interested in.
I should have included more information about me in the original post, but your post was very helpful -- thanks!
I'm not much of a traveler, and am pretty much looking to chill out while experiencing something new. (I could spend the summer in NY watching T.V. and porn, but it's a "been there, done that" situation.) It's also important that I not spend much more than I'd spend living in Manhattan. (I'm not sure I should even be taking a vacation because I have a negative net worth, but if it saves me money or costs about the same, #yolo.) Finally, I'm in good shape but don't want to sacrifice creature comforts, so I'll be eschewing hiking, backpacking, and the like -- I'd prefer to mostly veg out, read some books, and just wander around town from time-to-time.
I'd rate my priorities: Safety > Cost > Entertainment. Thailand seems to be a frontrunner based off the reading I've done so far. I'm still not sure, though.
And finally, not to be racist (xenophobic?), and I'm not sure where this is coming from, but I hadn't really considered India an option. I just imagine extreme poverty, overcrowding, and inescapable foul-stench -- but maybe I'm wrong. To be fair, my worldview is based entirely off what I saw in Slumdog Millionaire and negative stereotypes I've heard, not personal experience.