You have a real estate portfolio that will allow you make some great choices for you, your family and kids future.It sounds like your plan to have your SF area SFR cash flow at $2k per month is the biggest bucks for the bang (of the hammer). 

I don't as I am in Milwaukee.

Frankly, I got licensed in 2015 because after 7 years of investing in Milwaukee, I had worked with a few okay agents, but I felt most of the time looking at a property I was the more knowledgeable one of the two of us. 

Is the person genuinely interested in helping others, or are they simply looking to make a quick buck?

If everything but the intake checked out, I'd ask them (or your handyman on the other little jobs) if you can give them an extra $50-100 bucks to make a cheap, screw-in plate of some sort for the filter. 

For example the Average price per square foot to rent in Milwaukee, WI is $1.42.

And is electricity really just 20 bucks a month in the Florida summer?  

Hi there,I was supposed to close a house last week in Milwaukee.

Goal was to buy and hold this one.After checking comps again, looked like there was enough meat there to flip it and make a few bucks so we're trying to sell it right now, but we'll see.

Carrollton or Plano will get you more bang for your buck