@Jared AdamI would suggest taking a step back from forcing yourself to do a rigorous routine every day.

Just regular maintenance.

I had no malicious intent I just thought I could get cleaners and maintenance guys, 1099 them and not have to worry about all of the administrative fees and payroll... boy was I wrong. 

Even the best PMC may make mistakes or have a different idea on how to handle an issue than the owner (maintenance is #1 example!).

Like Joe, I personally subscribe to the strategy of putting as little money down as possible (hold onto your cash for future maintenance and other opportunities).

Thanks Matthew, do you do any special maintenance for the asbestos, like painting over it?

Is there potential to raise rents even more due to deferred maintenance / lazy landlord not adjusting rents to market rates?

Having said that, to maintain the yards in the summer and snow shoveling in the winter, I’m considering levying a $20/month yard maintenance fee to take care of it all.  

In this case, you really want your cash flow to be closer to $200/mo for a Single Family Home (SFH), and that should be pure cash flow (after your expenses, maintenance, vacancy, P.M. fees, etc).

I've only had to put in about $1,500 in some plumbing, water heater, and HVAC maintenance issues and I gained a tenant paying $750/month with very little effort.