Work your 9 to 5 for several years and in your free time grow your real estate business on the side.

But because he raised rents each year, and rents were increasing by ridiculous rates, tenants constantly moved, had to sell the property at a loss several years later due to constant vacancies.Finally, the most interesting situation I ran across was a tenant, a 93 year old tenant paying rent on a 2BR apartment for $90/month.

There are several objectives on this investment:  A. 

I used to go to them all the time with my dad growing up and have gone to several as an adult.

I have several rentals that I can sell with combined equity of 600k+.

However, I should note that this tenant has been late paying rent several times recently, which has added some strain to the landlord-tenant relationship.How would you approach this situation?

If it looks like you can subdivide, then you can sketch out a preliminary plan or several variations to give you a sense of how many lots you can build.     

you're going to be INvesting for the first few years... rental income from the property isn't going to start paying back what you spend in closing costs, rent ready costs, stabilization costs, down payment, etc. for several years at a minimum.hope this helps - not trying to be negative, just realistic. 

To clarify, I have been studying real estate for several years, but have been otherwise engaged in operating  other businesses that my wife and I both own, both as CFO and CEO roles.

Still use paper method for mileage logs.Tried QuickBooks several years ago but it was more complicated and I did not need the bells and whistles.