I would hate for this all to work out and the tenant qualify to buy the house only to have it fall through on a bad appraisal 2 years from now even though I bought this house with the intention of holding for a long time originally.This is my first post on BP about a specific deal so please let me know if this is the wrong forum.

That seems to work out fine though I'll need to make some decisions soon regarding replacing the furnaces with new ones or providing each unit with their own separate HVAC. 

As it turns out, this property will not work out, but we are on the case of three others already.

Yeah you can be leveraged 75% on every property but if it costs you $$ every month - then that isn't going to work out. 

How did that work out again?

We did that on this deal and made another offer, at that time the seller finally countered and we were able to work out a deal.

It would be too advanced and capital intensive for the beginner state I’m in now.

As a beginner investor in the Chicago area, it's really cool to hear about creative deals that work out like this near the region.

For the rent repayment work out a payment plan as to how much they will pay you back every month over the next XXX months.  

The numbers work out much better for us.