Is anyone aware of any of a property management tool that allows PMs to give discounts to tenants who enroll in autopay (similar to how major US phone providers like do these days)?

Has the market there provided good cashflow?

More likely is that they have been 'touched' by a many people providing the same service and narrow their selection to the few where they formed an favorable impression.

All that to say, I'm not sure when they will want to cash in and sell the lot due to the appreciation the subdivision has provided.

This is a physical asset, not paper, and it's providing consistent income.Albeit for your not understanding tax laws and depreciation, I'm wondering why there's a question as to what you should keep.You understand capital gains, but I'm pretty sure you're not familiar with depreciation and loan paydown.

An LLC when properly formed and administered provides separation and protection of assets that are outside of the LLC from the actions of the LLC.  

Quote from @Stuart Udis: I am always skeptical of these real estate "gurus" and course providers.

I’ve built relationships with brokers who specialize in Harlem, and one of them brought this off-market deal to my attention.

and for the life of me I cant see what these guys do that a very good RE broker who specializes in those assets could not do for you and far better frankly. 

For many years I was contacted by the housing office to provide input of my rents, both Section 8 and market rented units and participated in their annual surveys.