Hi - One of the questions to ask your self is "How come thousands of people before me didn't choose to register that name when it dropped, have I really found a nugget of Gold that everyone else missed?".
This is because the vast majority of hand regs were in fact registered in the past, and let go (dropped). So when it dropped no-one else wanted it. Check out it's history on archive.org.
If there is no history and you are the first then consider your chances of selling it. Who else is going to want it and how will they find it? Alternatively if you have a list of targets and intent to outbound then consider which other extensions have been registered. If you are buying the .com and the .net, .info, .org is taken then there might be a case for selling it as an upgrade to them. You need to do your own research.
If you are a speculator then finding hand registrations to hold for a long while whilst technology catches up with you is a plan. Finally chasing hot trends with hand regs might work {edit} but after the trend is over is it really worth holding it?
Good luck.