What should be my 1st step? 

You just took a big step towards starting off in real estate investment.

Although I am nowhere near Maryland, I wanted to welcome you to BiggerPockets and to commend you for taking the first step in your real estate investing career...and that is reaching out to experienced investors on BP for guidance.We are happy to help in any way we can, Matthew.Once again, welcome, and I sincerely wish you the best in your real estate investing career!

You can't change your business practices from one client to another.

What steps do I have to take in order to qualify as a section 8 landlord, if any?

My friend just contact the sponsoring broker who proceeded to say she was requiring a $1000 sign on fee to cover many things, I'm aware of MLS fees but is this normals practice?

I need to learn Subject To and Lease Option step by step from setting up my business to closing a deal with a seller and buyer.

Are there state/local legal factors in place that could preclude me from successfully practicing wholesaling in the area? 

I am finishing up rehabbing my side of  the duplex, and looking towards my next step... and I am not sure what direction that step should be in. 

I started by listening to the podcasts and reading the blog to get an intiail understanding and some direction on the first steps I needed to take.