It has minor upkeep expenses about $500 monthly taken care by the occupant.

That said, I believe that the profitability of short term rentals will continue to decrease until maybe only the industry heavy weights or the owner occupants can stay afloat. 

Hey Pamela, In my experience a good property manager is worth their weight in gold.

How much are each of them weighted?

He doesn't want to give the money back so my GC ends up keeping the materials and eating the 3500 dollar loss.

Bonk yourself in the head or snap a rubber band against your wrist any time you start thinking of price per square foot; price per square foot only carries weight with consumers trying to fight appraisals, not with appraisers. 

Obviously giving more weight to the agents opinion in a market I'm not as familiar with.

After speaking with the seller, who is an 72 year old real estate investor looking to move on to the next chapter of his life, he give me some information about the property: rent roll is $103,000 annually, occupancy is 100% and currently there is a wait list, there is no property management company (he manages the property himself), cap ex, insurance, and taxes are roughly $21,000. the 20 unit complex is split among three building where two building have roofs that are eight years old and one building's roof is 18 but "in perfect condition", each tenant is responsible for their own water, sewer, electricity leaving the seller only responsible for taxes, insurance and upkeep. 

The excellent information that @Joel Owens shared is starting to carry great weight.

It was recommended that it's in your chosen field and while there is some weight put on that it's most important that your new job is both full time and permanent.