Are hobo's really enlightened and have it together more than the rest of us?

no because they are on the streets because they cannot maintain their financial state and therefore end up losing their credentials eg:houses, cars etc.

Another Answer:

No. Hobos are not enlightened and do not have it together. However, Hobos have learned to survive while living a different lifestyle and have a number of totally different experiences from other people. As a result they may know many useful tidbits of wisdom.

On the whole, Hobos do not have the useful skills for making it in today's world, otherwise they would not be homeless.