May investors with an 8 unit building will consider an Umbrella over that location.# 2 & 3 are really personal preference and your specific risk tolerance.#4 - I just quoted some 8 units for 2 separate investors and the quotes are coming in just under $2k per year for Replacement Cost and $1M General Liability 

Consider an option though that will also include the added perk of allowing your tenant's on-time rent payments to be reported to the major credit bureaus; this creates just added incentive/point of positive reinforcement to get them to make those payments on time and transition to a system that is easier for you.

It is a bummer that my financing has to be so creative as that means I am not what I would consider an A+ buyer.

In the current market in my area I don't think many people would bother to consider an offer that was not on the standard contract- it would be too much hassle.

Might the Seller consider an even lower Offer than $149k (given the facts)?

But that also depends on what one considers cash flow.Given your limited time, you may want to consider an alternative approach... buying turnkey rentals; partnering with another investor who has the time (to find and run the rehabs) and who is also buy and hold oriented...

You might consider an S-Corp for your flipping, especially if these flips will be short term.  

You sound like you're new at this, and if so, you might consider an inspector.

Anything less, I would consider an acceptable area for buying rentals.

And the following is why.Which brings up my question for the day: Twice now, and unknown to me, my agent called the listing agents on 2 properties _before_ she showed me the places, to ask if they would consider an offer that was $40,000 below the list price.