To answer the question in the first post as to which would be easier I'd probably have to say being happy whilst being poor. Sure, you can be happy either way, with wealth you have the opportunity to buy the things you want and make people happy around you, but you can also do that if you are poor and will usually be more happy when you buy it because you know you worked hard to get it.
Either way, I think happiness comes from helping others, it's pretty much impossible to be happy alone.