So, would you really need to find a property that is just outdated and needs cosmetic updates in order to get a loan from the bank and based of your numbers when analyzing the deal it would have to be substantially under market value?

I have a savings account and a somewhat substantial 401k.

The fortunate thing in all of this, they really are neutral (they get paid whether the loan funds or not :-) Ideally I would start it off as legitimate learning effort and ask them what factors are influencing, because you really thought that it was most comparable to the house next door.

When the property transferred it uncapped the taxes and they increased substantially and ate up all of the cash flow. 

Significant, but not substantially.

But as I grow, I know that there's a substantial need to be better at analyzing properties.

All this being said your growing substantially faster then I have using it.

A GC can also get busy with other jobs and put yours on the back-burner if he's not making a substantial amount from your project (or even if he is).

There are really so many personal decisions that will influence that choice on refinancing.  

If you have 5 to 10 homes in your portfolio, it is possible to get a mortgage, but it can be difficult.In 2009, Fannie Mae increased the maximum financed-property limit from four to ten.Most banks won’t offer a 5-to-10 properties mortgage because the process of underwriting the investor’s mortgage application can be very hard work.To finance a home via Fannie Mae’s 5-1o Properties program, there are many criteria that must be met, including a minimum credit score of 720, substantial down payment requirements (for purchasing) and equity (for refinancing), no bankruptcies or foreclosures in the past 7 years, and more.Real estate investor mortgagesIn 2009, Fannie Mae rolled back a mortgage rule that prevented real estate investors from financing more than 4 properties at once.At the time, investors were limited to 4 properties financed, which included their primary residence.Today, the maximum number of allowable, simultaneously financed properties is 10.