Our last two projects were in the mid 70% cash on cash range which we consider an outstanding return. 

Also, I would suggest driving for dollars in certain neighborhoods that you would like to invest in and write down the addresses of the properties that are eye sores and appear to not been fixed up in the last 20 years then find the owners names, skip trace them and then call them to see if they would consider an offer? 

Since your business is going to be in the new property, consider an SBA loan.

I was hoping to get more insight on at what point should you consider an llc.  

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in a an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is likely to be higher, then you may consider an umbrella insurance policy.

Or, since I believe the rents were significantly undervalued 9 months ago, and may be even more so in today's market, would they consider an in-house/updated estimate of market rents. 

So, we'd have no problem politely, yet firmly, asking the tenant for proof of their son's death.We'd also politely tell them we'll start the eviction process when they fall behind on their rent, but are open to consider an acceptable payment plan proposal from them to avoid an actual eviction.

For a short term rental you also have to consider an amount for furnishing and management. 

Trying to find what I consider an "acceptable" deal. 

Now consider an HVAC going out.