It's like politics or religion, the longer the conversation goes, the more entrenched they become in their side or views, and same for you. 

The tenant will know the downside so no need to share that but there is a risk that a quality candidate might bolt if this is viewed as an unearned punitive gesture or threat.  

I think he naturally has an optimistic point of view when it comes to real estate and forcing equity into distressed properties.

That will determine how you view deals and their numbers.

I always highly recommend all my clients start with a four unit from a financial point of view however some people value lifestyle over their financial freedom so I find that often times families will pick SFR's or duplexes still over 3-4 units.Additionally, 3-4 units have more stipulations now than they did when @Ryan Hurd bought his fourplex.

My pitch book has evolved over time, but the 3 things you need to answer for the investor are: How much will the investor getHow will the investor get paid backWhen will the investor get paid.I have some investors who only want to know the high level view, so I include an executive summary of maybe 3 to 5 bullets explaining the opportunity. 

I don't think that they want to be reminded of this by their landlord; handing out cards for free food would be such a reminder in my view even if they are depicted as representing free turkeys.

Schools are not great as far as I can tell, but in my view it’s one nice beach town close to NYC where you can find relatively affordable properties.

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From viewing this I think the best way to approach this is to have a hard conversation with her to start to let her know that this isn't a free ride and you are not a bank.