Maybe one of you can help....I run a property management company.I have a new prospect that wants to go through with a contract.

Shelly and I have always been driven to help people, especially those facing tough times.

This can help you cover your mortgage while you build equity and gain more experience managing multiple tenants and building out better systems and processes if you do decide you want to pursue larger properties. 

However, if my old college friends want to live with me and help with the mortgage I thought it to be a great house hacking scenario.

We can certainly help with this scenario.

@Michael Plaks, information on the link you sent was very helpful but as you said, I can't get a clear picture what I need to do on my tax.

I'm in the union on long island so I have a decent W2 job to help get started, I think a house hack would be my best bet starting out but, what do you guys think?

Hey Chandra, applying part of the rent toward the purchase price motivates buyers by helping them build equity.

Then 4) I would get laser focused on 1 or 2 good markets with a realtor that is also experienced with flipping and can help you find good deals. 

Hope this helps get you started!