Would have done 2-3X better in stock market, and with 1000% less grief/stress. read this to start with Why your house is a terrible investment - JLCollinsnhAlso, big picture, residential RE, appreciates only at rate of inflation, on average both in US and abroad."

Storm damage would commonly be covered by your homeowners insurance.10.

So I snap pictures of paper receipts in the store and send it to that dedicated email.

It's all covered in his fees.  

Our insurance company (State Farm) doesn't cover flood, so our flood insurance policy is through FEMA's NFIP (national flood insurance program).

I use one unit as my primary residence and have been using the other unit as a mid-term rental (~1-3 month stays) to cover the majority of my mortgage.

In my head i picture a some empty room with a printer on the floor and stacks of paper everywhere, having to drive to the post office and handing them a list where they hand type every address one by one. 

I'd minimize the risk of having negative cash flow in the first 12 months when things are the most unknown and I'd be able to increase the gross rent of the property which should give me a better loan or at least bigger margins to cover my risk for negative cash flow. 

We have a fee for this in the lease but how do you cover for this in the lease ?

It's likely coming.That just about covers it.