I want to stay on the north side, but I'm open to areas outside the ones I mentioned.

You mentioned that, "unless handled at arms length for retail would probably result in a step transaction".could you explain what you mean by this? 

You mentioned you want to “continue to build equity through the debt”.  

@Andrew Johnson covers a portion of this as he mentioned factoring in his rehab cost during his initial stages, not sure if he's referring to long-term property holds of 20-30+ years.Also keep in mind these strategies will change based on property type, SFR, Duplex, Quads, etc... will be treated differently than a 20 unit building, which will be treated differently than a 120 unit asset, and so on.... this will also get you different replies to your question as the different debt structures will fulfill different requirements of the investors.

They mentioned about wanting to re-up their currently lease by signing a long-term lease. 

As I mentioned, this is my first analysis so I’m trying to understand the inputs.

Caleb, I forgot to mention that I do have a job so I probably wouldn’t need a co-signer.

You mentioned you don't want to give the banks your SSN to start the process.

I forgot to mention something important. 

If my house appreciated by that much I would do what you mentioned and buy new investment properties.