My next goal would be to invest in out of state short term rentals and add those to the portfolio, but not sure how that would impact my LLC if I create a Wyoming Trust/Holding Company/LLCs and foreign file for incorporation into Connecticut to complete the first deal for the duplex, but then what happens when I want to invest in out of state investments deals/opportunities/homes? 

Pay attention to the changes being proposed to the County's STR ordinance.

In addition, I live with my parents so even househacking will still cost me over $400 a month, which is what I pay to stay with my parents. 

Craigslist or Facebook marketplace did came to our mind at first but we are afraid to find someone who would randomly stop paying rent and become a pain to evict. 

Now you need to figure out how to find deals and pay for them.

I was thinking it may be closer to a "wash" or, maybe only slightly more only bc w/ a duplex at least we aren't paying for two exterior wall materials for two sfh?

Do you pay closing costs to them? 

Pay for the subsequent tax bills for the following 4 years.

That said, the realtor says he didn't have a contract with her and does not need a contract with me either and he works based on trust.

Quote from @V.G Jason: Quote from @Chris Seveney: @V.G JasonI saw today that 30% of jobs now in this country are federal government or government contractorsWe cannot live off trillions of dollar deficits every year - employment is actually negative this year without the government.People lose jobs = cannot pay homes = homes get sold at discount = reset appraisals / lending… You're not wrong, just the sold at discount part I think the floor is going to be higher than people think.