Also 4th quarter of last year Packwood and county officially did discuss potentially regulating STR's by either limiting numbers or adding a tax to cover increases in local services that are needed. 

I assume you mean that unemployment was 5.7% not 22.2% haha, but are you just talking Pittsburgh Metro, or Allegheny County?

In addition to my surrounding area of Bridgeport, I am also open to looking in New Haven County, Middlesex, and Hartford as well as an out of state market (Detroit, MI). 

You can probably just go ahead and live in that 5th unit, but I believe whenever you go to refinance it with a bank or what not, the 5th unit will make it require a commercial loan and not residential regardless of what the county records show the property to be. 

Each state and county has a different way of finding out, but it should be public info in each county.

I also received a letter from the county saying that my property is in violation of several health and safety codes. 

It looks like according to the county site (sbcounty.gov) they require all renter payment go to the active owner. 

We actually have our main meeting coming up on January 14 and a county meetup in Clermont the following week .

I believe Alexandria city allows it but portions of Fairfax county do not allow it. i would go option 1 personally. 

Also calling the county and asking them who some use as consultants could be worth it.