Jimmy,You need to show (2) years of 1099 SE income in order to use FHA, or traditional financing to get approved for a mortgage.

I do not know him, but the path he is leading you is a difficult path    Note difficult does not imply impossible; there are people who are successful with S8 housing    In my area s8 is so undesirable that they write laws trying to make it challenging to not allow S8 tenants.  

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That is probably a good start to setting the goals you need to achieve to make the dream happen.

I am currently trying to break my analysis paralysis. 

Welcome to BiggerPockets, Zach! 

We have told my ex-wife that we are willing to let her stay in the house for a time but she needs to pay rent.

If you have cash on hand to fund the rehab and want to extract it soon after the project is done, you can use delayed financing.

Partner Driven identified the property through our direct-to-owner strategy.

Going to the events page above and seeing who is hosting meetups along with connecting with people at these meetups is a great way to grow your network of people within a small 25-50 mile radius.