For example reminder to replace HVAC filter every 3 months, to ensure pets are vaccinated yearly, to ensure tenant sends me copies of renewed vehicle registrations and insurance etc.

These properties are all within 1-3 months of completion and the investor does not close until the CO is revived.  

Do you mind me asking how much rent you charge/month?

He will be eligible for Medicare in 6 months.

Hello, A few months ago I wrote about how I was done procrastinating and ready to get in the game.

You don't need to know everything to get started; you need a foundation to build on and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

Ask for any records of fires in a given zipcode over the last X-months. 

It currently has 14 out of 17 units occupied, generating a monthly income of $6,300.

Would it make more sense to live in old side and work on it while living there and still make rent on other side while losing out on being able to claim expenses as tax deductible or live in updated side and loose out on rent for about 4-6month(1300/month) but be able to claim all expenses as tax deductible.

If your monthly budget for this type of thing is $100, you're losing money.