However, I'm already  $helling out on software, marketing, branding, etc.... so tell me, IS THE JUICE WORTH THE SQUEEZE? 

My buyers of my new construction homes even get sewer scopes to make sure the line was put in without any belly's.

My wife and I are experienced with LTRs in town, but given the location of this property we think there’s tremendous potential in the short and medium term market, we just don’t have the experience/data to know if the juice will be worth the squeeze for furnishing the place.

Sewer line check for bellies, cast iron/ old clay/ offset lines, broken connections, roots, mud in lines, main tap. 

A large belly filled with mud?

I do 12+% below actual fmv belly to belly with off-market sellers. 

I do think you’re trying to squeeze too much juice out of one property with that boarding house/air bnb idea.

Any one of those can override the other two, but obviously a little juice in all three buckets is ideal. 

I think we can reasonably push that over $340K (with 7% both cap rate and CoC), but I'm not sure if the juice is worth the squeeze with a 20% down payment of over $600K. 

Not sure the juice is worth the squeeze for all of the capital and labor invested versus the cashflow you are going to receive.