Wanted to do a 1900 sf main with walkout basement house for my family instead of a 1600 sf home on a flat lot...that I would ultimately sell at some point. 

Hey Josh,I tried Propstream for a little while and then ultimately ended up choosing Batch.

I understand they serve as a benchmark when calculating the discount rate but I see people try to predict them on a 10-year basis which seems incredibly difficult for first-time investors and ultimately, we never know what they will be. - Adam

I considered taking the negative one one and allowing another existing property profit “balance out” the cash flow, but that feels like a bad move and would be better to sell  My ultimate goal is to build cash flow for FI, which I need more to do. 

I would say yes because it ultimately effects the borrowers DTI which raises or lowers their purchasing power 

But ultimately, mistakes and problems will come no matter how much learning you've done. 

It might be that the number doesn't even factor in interest if he gets a total price he would like.Remember to listen first and you will undoubtedly come up with creative solutions to take care of the sellers needs while ultimately getting the property you want.

So where does one begin if the ultimate goal is to become a financially free investor?

This will ultimately depend on the property being marked as rural or not on the appraisal report, and depending on the population density, the lender may or may not finance the property.

This will also tell you where the bar is set by your competition because that ultimately will tell you what kind of furnishings and amendments you'll need in order to be competitive.