Cash on Cash is the % of the return ( your profit after expenses) against the amount of personal money you have invested in the property. the less money you have into the property and the greater the profit the higher the cash on cash % will be.

The sale would make me whole from the capital and also include profit.

Based off a loan amount of $78,400 at 6% interest and Annual Property Tax of $1,280 and Insurance $750, your payment would be approximately $639.21 Factor in 20% percent for vacancy, repairs, and property manager fees and your left with $752 for a profit of $112.79. 

Wholesaling profits will definitely be put towards my first investment. 

I want to generate monthly cash flow so I'm thinking buy and hold (rent). 

I figured that I could buy them, fix them up a bit and sell them separately for a larger profit.

So you are buying the deed, however it is redeemable  which simply means the owner at any time could come forward and say they want the property and the owner would then be required to pay you whatever you paid for the redeemable tax deed and a 20% penalty profit.

I use a 3rd party service that allows me to request the prospective tenant pay for their background check online and then the 3rd party will generate the background check and send it to me. 3) Well, in that case, you are in a tough spot.

Currently i have been looking for a property that puts $200/door in my pocket, since that is what my single families net me currently and after running the numbers, im just not finding these prices... ive made 41 offers on multifamiles this year so far in 2018 with no luck yet, am i just asking for to unrealistic of a profit from these?

So it allows for cash flow/profit at year end- but a tax loss on paper.