Windows can be repaired, I DIY but someone should be able to fix all your window issues for far less than new windows that won’t match the rest of the house.

Your goal is to match apples to apples (i.e. sq footage, #BR/BAs, amenities, style, etc) as closely as possible. 

The home is listed for $110,000 but homes that have sold recently, sold for over $155k matching lot size, square footage, and bed and baths. $2500 is to cover basic repairs. ie paint and other aesthetics.

I think the main distinction is Short Term Rental vs.

I check to see how many meters...if the number of meters (or plus 1 if common area) doesnt match the number of units, Im skeptical of the legality of the property.Did you use an agent to purchase the property?

My guess is that they gave you first shot of increasing your offer to match the loan contingency offer. 

How would Syracuse match up for a long term buy and hold strategy, in your opinion? 

Since our current tenants move put at the end of this month, we willing to test out the STR gig for a couple months and put it up for LTR next summer if the returns don't match the workload.

Look at what the other rentals look like in that area that are getting the higher rent amount and match the quality or your rehab to theirs in order to get the same rent. 

Most realtor are lazy and just send me a generic list of their listing that don't match the criteria I told them I am looking for.