Getting that price down is always going to be your big money maker, ahead of every other consideration.

I also went ahead and purchased my domain name for a website which is also suggested, but not mandatory.

Is there anyway I can vet the tenant before I go ahead with the purchase- verify some income, past evictions, felonies, credit, past landlord testimonials?

If you have multiple properties you may be able to "stack" your coverage just like you can with vehicles. 

looking to plan ahead for next year.  

My partners DON'T think about scalability and that became a  problem.However, since they defer to my guidance as the most experienced Partner, I implemented several scalable solutions ahead of time.For instance, don't buy a rental and NOT use a rental collection website.

I have 14 separate policies with them right now for vehicles, umbrella, personal and business insurance.

I called the city to get ahead of the issue, and this is where the story takes a dark turn.

I've long thought that agents can up their game when it comes to service and skills, and there are some underserved niches in our area, so I went ahead and got my license once REAL came to Illinois. 

If its not much - maybe you want to limit it to one LLC and registering as a foreign entity in all the states you do business in instead of opening up multiple LLC's.You likely want to consult with an attorney before you go ahead and set it up so he can tell you what liabilities you would be protected from when opening up an LLC.