I have sufficient funds to purchase the property, but struggle with knowing whether or not I'm growing things too fast.

Will re doing the  properties siding and some exterior upgrades be sufficient enough to force the appreciation or is the only way to increase the appreciation is to rehab  each unit?

Use the flipping to build up a war chest that you can deploy when it's sufficient to buy you some scale.

I want to buy the house likely before I have any sufficient income for debt/income purposes.

Secondly, will the property provide sufficient cash flow that meets your criteria.  

As long as there are separate entrances and sufficient privacy, make sure you're within code. 

Research, raise your RE IQ, hang around and listen to people smarter and more successful than you, quality is better than quantity, know your limitations financially and mentally and at first take it very slow and dip your toe in the water.

You could try that, if you do sufficient background check on the renter and feel comfortable. 

Provided OP will owner occupy and there is sufficient equity in it, this can be done with <$2k cash to close (inclusive of down payment and all closing costs) and no PMI.

I am not getting in younger so I want quantity.