Cashflow may be minimal but rates will go down eventually, and at least in Coastal FL, values will go up (even higher). 

Both times I ate the expense of repair after the neighbor eventually had the tree cut-up and removed.

Is it feasible to get $96,000 in cash eventually from the second cash-out refinance in this way and keep expanding wealth in this way?

Securing a premium investment or dream property is always going to take some work, effort and overcoming eventual disappoint.

I aim to apply my real estate knowledge to build a portfolio of rental properties, starting with single and multifamily homes and eventually expanding to apartments.Should I pursue a degree in financial planning or accounting to complement my minor?

However, I would like to build connections and eventually start here in California.

If it's landlocked you may think you will eventually be able to get access through a friendly neighbor, but no, that's not ever the case.  

I plan to eventually have just a few units. 

Eventually someone will ask "Well ho much money do you need?"

Tough decision but eventually went with Digb because they also help with taxes and planning.