I'm a first time investor and would like to "house hack," so I can establish residence there and at least cover the mortgage with the other rooms.The real questions that I don't know how to answer are the due to the fact that I'm a 1099 and have been for years.

Your loan for your unit is more than $250,000 (which is the Max your lender will likely require) they could ask you to cover the $50K.

In that case just cut the shower valve area out replace with the one you desire and cover with cement board. 

I had less than 3 rentals for over 5 years and covered under umbrella insurance, also because I was self managing them and doing have work myself which the LLC won’t really cover against (ie the LLC would be solid but if I personally repair something or do the lease/screening wrong as the property manager they can just sue me directly).

One coat of paint won't hold up for long in our location and may not even cover the paint that's already there.We've been replacing gutters over the past few years, all of which are baked in same color of which the community is already painted. 

Make sure everything is spelled out, cover the details on each scenario, if it all goes well, and if it goes south. 

I thought I had everything covered.

I have a couple of suggestions:1. if you are doing a rehab that will include the wiring, you may get a Renovation Builders Risk policy to cover you.  2.

Below is an article that I thought covered some most of the bases, but I have no way of knowing if it is good advice or not since I have not done it.  

In NJ, tenant will cover all count and lawyer fees for landlord?