I have always loved real estate and would spend lots of bonding time with my dad, driving around wherever we happened to be, looking at houses, playing "guess the price" on the for sale ones, and dreaming about owning this or that, or having a rental here or there.

Local factors are all still strong, but interest rates do make a difference at every price point. 

You are not spending the money this way, you are using it.Multiple uses, but a one time cost, makes the interest rate a non-factor...so long as the first investment covers the expense of its use.

I have excellent drive and motivation, and I feel my background in banking gives me an advantage to understanding the different types of loans and the finer portions of the lending aspect, since most people seem to finance homes. 

As I'm driving for dollars I come across plenty of fire damaged properties , how should I go about estimating rehab cost?

Drive towards a solution where you and the tenant come to an agreement and try to remember that he's human...driven by emotional reason. 

As for records and PM, just google drive.

Looking at cash on cash, IRR, value to be added, sub-market opportunity and trends, tax advantages, etc are all important factors. 

Is a half-circle drive in front doable?

When you start borrowing that much money through multiple HELOCs, the limiting factor tends to be DTI, not equity.