The fix and flip business would report $40,000 of ordinary income.Your contractor business would report $10,000 of ordinary income($20,000 of income less $10,000 for supplies).Total combined income of $50,000.you brought up a good point with the licenses.

I totally understand that he's likely not going through every e-mail individually. 

Total Repair Estimate?

I have about 5 credit cards, not tons of debt maybe $12k total between the 5....

You NEED that total number to be less that retail price, or you need to walk away. 

Both tenants looked to take good care of their spaces - house was in fantastic condition.David -- from the research I've done in the area the rent he currently charges seems on par - but I am totally going to check out rentometer - thanks so much for the tip.

Total newbie here....been renting my entire life and finally (at 33 yrs old) realizing that my military Basic Allowance for Housing (BAH) could be building equity and become a rental property instead of being put in someone else's pocket.  

you can shop with another lender, and see if the totals come out the same. 

I would certainly not rely on venture capitalists to start a business again.

This was also in rural NY not Chicago so your mileage may vary@Brie Schmidt brings up an interesting point about the zoning may now be single family, if that's the case do you want to forever and totally make it a SFR?