When I dig deeper, I noticed that almost majority of these properties had one thing in common.

Is it just the emotion of it being your grandfather's house that is driving you to want to keep it?

I would encourage putting your emotions about the home aside and viewing this from a strictly financial perspective - Are you really better off in the long run trying to keep this home?

But I did end up digging much deeper into the midway oval and it’s exactly what you described.

Some of the statements you put in your original post make me think you have some kind of emotional connection with this tenant which is a big no no..

As you can probably imagine, becoming emotionally attached to this home is super easy.

and the letter might be more for someone emotionally tied to their house, not a income property, but hey, no real harm in trying!

Then, I can do deeper analysis if need be.

"I am leaning toward a $100/month reduction" You are leaning in the wrong direction by allowing emotions to drive your business.

I could be digging myself into a deeper hole....All the people I meet at networking events want to work together by being my cash buyer since I'm already partnering with 50% wholesale fees (me being in the acquisition and my partner to find the buyers and close).