Please get some help with this. 

It does appear that we need more information about actual ability to pay the rent but in reading between the lines it appears that there will be two more adults living in the property, so we have more information to gather.

The 50% rule - in my opinion- is used solely as a quick back of napkin calculation to determine if it is worthwhile to do more investigating of a property. 

This is incredible detail and more than I could have ever expected!

@Cameron Moore thoughts on this?

I've got about $525K in equity in the property, but lenders have told me that I cannot get a HELOC to access that equity for additional purchases because the duplex was financed as an investment - they have said TX law dictates that HELOC can only be used on primary residences.

I am in one of the higher tax brackets and could be saving around 40k~ a year on taxes with this.

Looking to connect with people in the Boston area!

There's no right or wrong way to do this, but long distance deals with contractors can go badly in many ways, probably more horror stories than success stories. 

If you actually need to do permits on everything or just structural fixes and big items (I.e. roof, siding, windows, etc.).