My question is, could the city be responsible for this situation?

Too risky for us.Regarding additional guest packages, you can easily change your tax situation by offering what the IRS calls "significant services".

Considering doing a 75% cash out refinance > 30yr 7.45% interest rateIn what situations might the 50% Rule provide a misleading picture of a property's financial health, and when would relying solely on the DSCR potentially overlook important factors? 

What exactly does the realtor do in this situation?  

However, I received some feedback from one of my partners that the play here would be for an investor to subdivide or re plat the land for a multiple tenant situation.

You pay your agent at closing (think of it as an additional closing cost) Depending of the situation and of these options can be used by you and your agent to negotiate with the seller.

@Jarret Jarvis  Boiler or Central air conditioning does not have to be an either/or situation. 

We were in similar situation 2 years ago.

What is his situation? 

There should be some financial advisors or real estate attorneys on here around your area who specializes in hospitality ventures and might provide valuable insights tailored to your situation.