According to him we may have a leg up because the decision was based on them being "model tenants", and that no longer applies.

Over the past 6 months I have been cramming as much knowledge about different investment strategies and have been extremely excited that i have gotten the chance to apply what I've learned and create some passive cashflow.I have 3 current buy and holds and would like to acquire 2 more before the end of the year.

I finally decided to apply what I've been learning about, gassed up, and got to to know a neighborhood a little better.

You probably won't be able to rent it seasonally if you plan to follow the 6 month > rule. 

Repellents containing DEET (N,N-diethyl-meta-toluamide) typically used as mosquito repellents are also labeled for use against no-see-ums and can be applied prior to exposure to the biting midges.

Caveat...all depends on what you know but with the 50% rule showing negative, the need for you to dump 72,000 in it,  and your optimistic outlook only showing 6%, i'd park my money somewhere else and look for something better.  

I'm inclined to lean more towards the idea that that's the exception to the rule, but it certainly shows that outcome is possible.

Would I be wrong to take 3 or 4 similar properties (1 story) and determine a $$/sq ft and apply that to the 4000 sq ft of a two story AS A STARTING POINT ?

Rules like the "2% rule" often force you into 20k rentals.

Yield maintenance applies n/a Is there a maximum loan term?