If your friend recently made 3x his mortgage, but it was a spring/summer month, he could easily struggle to cover the rent in the fall and winter months. 

Do you know any private landlords who have been sued for more than their insurance would cover?

Additionally, covering unexpected repairs and meeting lender requirements can pose obstacles, especially for newer investors. 

@Clayton SilvaI think you covered a lot of the angles - the answer is “it depends” - every person is in a different situation and stage of life and some may want to pay points and others maybe not.Right now I would not be buying down the loan knowing the fed will lower rates, which should slowly bring down the 10 year T which would then lower ratesFor me I would guess I would refi within next 3 years so I wouldn’t pay pointsIf I thought I was not gonna refi within 5-7 years then yes pay points

Does anyone have referrals to residential cleaning services that cover South Tampa, ESPECIALLY if they are experienced in non-toxic cleaning since I'm house hacking my home?

We have actually agreed to cover everything you mentioned in your post along with all other necessary items to ensure you are purchasing a home that is suitable condition to be a successful rental. 

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in 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 expected to be higher, you may consider an umbrella insurance policy.

With an inspection, if it was something that was known to the seller, they may have priced the home accordingly (eg older roof, price lowered to cover cost of new roof). 

If, for example a judgment is rendered in 2014, it probably only covers through 2013 since the 2014 taxes aren't even due until the end of 2014.  

I need a second mortgage to cover most or all of the rest.