@Andrew Bang this is a good perspective to hear from a lender, as a lot of the BP community (at least us newbies) fall into the energetic, less money category. 

It appears the two of you have a different perspective on what type of relationship you have.

Recognize it as an investment strategy (seller's perspective) that generates cash flow from equities.

It is a very similar forum to this but you get a few varying perspectives that I found very helpful!

For a long term rent and hold strategy though where cash flowing is the goal, how does the market look from your perspective?

I don't agree with your perspective, even with asking this question.

Whether or not the lease says the tenant is responsible for the grass it's ultimately going on the property owner from a city's perspective.

If you do the math and show them how much they were "missing out on" (which is going to be very minimal) it will help put it in perspective, and I would imagine they won't care so much about the missed interest, and more so about getting back the original security deposit amount. 

I'm dedicated and motivated, and realize that this may or may not be ambitious depending on your perspective.  

I was looking at it from a tenant perspective and how often that threat is thrown around.