Now, one could argue that if you removed the financing component from home purchases, the market value of properties would be markedly lower, and I wouldn't disagree with that.

My reasoning is that I like having a lower required monthly payment in order to maximize my monthly cash-flow.Remember, you can always reduce your principal balance at any time with a HELOC (or an loan for that matter) simply by making a, "principal reduction" payment.

Is your rent lower or higher then the current rent?

I think holding in your personal name with an umbrella policy may be similar risk wise to holding the property(ies) in an LLC but with perhaps lower overall costs after factoring minimum taxes and fees associated with an LLC.Perhaps an atty could tell you what the process would be for transferring properties into an LLC, but I don't imagine it would be difficult. 

It's been amazing, and we don't mind the lower rent in exchange for knowing we get it early!     

Just know that getting more bids later on may come in lower or higher so account for that...for a first time flip just go ahead and assume you’ll spend more than you think.

Lets say you come in and lower the expense ratio to 60% and increase the rent to $450.

In the example you gave, you cash flow is 80% higher than your target and but cash flow is only 3% lower than your target. 

No clue who they are, but states like IN and OH will be better for lower taxes and landlord laws than IL and WI. 

You end up developing and refining systems that lower the risks.