Quote from @Cameron Moore: Exactly. 15 years ago, I noticed an increase in owners using insurance to pay for a replacement roof, usually to sweeten the pot during a sale.

My motivation is to increase my financial literacy and diversify into real estate.I have rented all my life and seek to become a homeowner/ investor to help my family and make their lives easier.

As long as you express the key details of tenant information, lease dates, along with any standard information to vacate, and clear language of "non-renewal".

In the meantime learn and figure out how to increase income/savings.

Tell him it's time to do a remod and as a business you hope to market the place at a substantial increase.

Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

Property is $6.5M, leased for 20 year corp-guaranteed with a current rent of $450K (10% increase every 5 year).

So the best solution is to buy a house needing extensive renovation for cheap and use that discount to change the layout when you bring it up to living standards. 

At annual rent increases, I do scour Zillow for market rents in the area, which I share with my tenants.

We have created work instructions for every step of the process so we can maintain consistency in how we evaluate properties, communicate with tenants, market our properties, handle rent increases, manage property turnover, etc.....