@Paco Rabi,It's definitely nice to have existing tenants in place because they will be paying rent as soon as you close!

I just let it do its thing and don't pay attention to the glitches in communication, or where the money is going.

At $200/month, that should get you about 25 hours assuming an $8/hour pay grade.

Always, always, always pay back your parents.

Owner-occupants can pay more since they are not looking for a "return on investment" per say. 

Have a lower monthly payment, not pay PMI, be able to save a bit more from the W2 jobs each month, as well as having a greater percentage of the mortgage covered by the upstairs tenants. 

You should focus on paying it off and keep in mind the more equity you gain the more of cash you get to keep.

Tenants insurance should pay as that is what renters insurance is for. 2.

Maybe that's the price I'll have to pay anywhere.

Quote from @Gian Pazzia: For properties that small, you should budget $450 per property and use cost segregation software like the one below from a trusted brand that has been in business almost 25 years.