A good consultation in this circumstance could be worth its weight in gold, plus a good lawyer should be able to give him clear options.  

The only time I've ever let a tenant barter their services for a reduction in rent was when I had a guy who owned a lawncare business renting from me.  

It seems like a no-brainer to me but I'm looking for someone to weigh in on how much of a difference it would make in the final sale price, or potential reduction of DOM, in a place like southwestern Connecticut, Fairfield County.The second part of this question is: if I hire the HVAC company to do the install, including the furnace, how do I adjust the original SOW and deduct the cost from the HIC?

You can use the Interest Rate Reduction Refinance Loan if & when you need it to help you out.

A good pm is worth their weight in gold.

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I suppose you could counter with a price reduction - or the buyer may cite that as a reason for a below-market offer, but that's still money out of your pocket, one way or another.

I'm still cash flowing close to $750 per month on it but even a tax reduction of $1000-1500 per year would be tremendous. 

I will be experimenting this sometime in the future to reduce the weight of vrbo/airbnb on my business.

Location and walkability will matter especially for anything close to downtown KC, the Plaza, or Westport areas--- as home values can change $50K-100K within a few blocks of certain areas---- though any reputable appraiser will consider the best "apples to apples" comps and weight them based on proximity to the subject property.If you are using private money, hard money, or other investment type loans, some of those private appraisers may look at the property through a more similar lens as an investor--- and focus more on the income potential of the property.I hope this helps!