I would say 1. Star rating 2. Location 3. Ability to extend trip 4. Budget When you say downtown, are you referring to the Financial District area? If possible, I'd prefer to be a little bit more centralized than that, although if push came to shove I suppose I wouldn't be so adamant as to forego compromise. I'm a little curious as to when you say stay Downtown to get an extra day. Are you saying that I could find such a price difference that I could pay the same amount for three nights at a downtown hotel as I could for two nights at a central hotel, assuming that the hotels are the same star rating? If that is what you're saying, I could definitely make that deal. Essentially, the priorities for this stay are tourism purposes. My finance has never been to the States and I want to show her New York. In order for the extension in days, I would say if I could cap it at around $400~$420 with taxes, it would be ideal. I am ready to commit now if I am able to find the right place, so long as I find a good deal.