Additionally, you will now have 3 houses (your primary and 2 rentals) that are appreciating, which is where real wealth comes from, not from the cash flow.

Additionally, If anyone would be willing to have a conversation about what they look for in CPA's and what they learned financially starting in the rental investing business I would greatly appreciate it! 

Not only will this add no additional protection, it will merely add operational costs.

I want to implement some additional verbiage in our rental agreement so this doesn't happen again and things are crystal clear to us/tenants who do end up being "month to month".

So, providing accurate and detailed information in your real estate listing is essential.To provide accurate and detailed information, follow these tips:Include information on the property’s size, location, and amenitiesMention any recent renovations or upgrades to convey the value addition that has gone into the propertyProvide information on the surrounding area, such as schools, parks, and shoppingBe honest and transparent about any issues or repairs that need to be made – nothing turns off a buyer faster than the feeling that they may have been lied toRemember, providing accurate and detailed information can help build trust with potential buyers and increase the chances of a successful sale.

So my question is, are there any creative ways to make this work for everyone so they can generate their cash flow free and clear while I am able to have a better cash on cash return and have additional capital to deploy later?

Depending on your personal life and your other properties, during the 5 year period you could live in 3 of your properties working towards this tax reduction.

This individual has successfully been doing property management through a company that has supported him in addition to his off-line unrelated real estate duties that he successfully continues to manage.

You can flip when you need to produce cash to buy properties cash or fund additional rentals.

This is a very broad question and without tons of additional info no one credible will be able to provide you a logical response.