I like the fact that one and a half units pays all bills.

Now, this would obviously be negatively cash flowing since you would need to pay taxes and insurance.

Not to mention, the right system will enable your tenants to pay rent online, have a tenant portal, and all the other features that both tenants and owners need this day and age. 

You might be surprised, but your rental properties have more in common with dividend-paying stocks than you think!

The property owner's tax professional can help them with that and ensure they don't pay taxes twice on the same income.Disclaimer: My advice/opinion in this post is just that, my opinion.

Property damage, excessive wear and tear, but paying, that PM has an incentive to look the other way, don't they. 

Who pays when the resident breaks the agreement and quits paying? 

If it is not adding up, and you can find an attorney specializing in that type of thing, it may be worth paying for a little of their time.

Now, you need to figure out how to find deals and pay for them.

The best strategy is to buy properties that need fixed up with hard money/HELOC, fix them up, the refi out to pay back your HELOC/hard money.