@Sandra Ho,I'm a little late to your thread, but you pose a good question—neither of these situations are ideal.

I simply call my broker and add the customers name to my liability policy.

We only have 30-40K down payment and are hesitant about 2 things:1) Investing into a property purely for STR... we would want to ensure it can still pay for itself as an LTR if need be PLUS ideally we would not invest more than 350-400K.

Likely more than most brrrr, but with an ideal brrrr I can make infinite return.  

There are likely at least subtle differences between those proposals.In terms of good and bad experiences, you won't find an insurance company that doesn't produce happy and unhappy customers.  

Customer service is A+.

My ideal property is a detached single-family distressed, 3/1 or 3/2 home in an A or B neighborhood with good schools, ideally in the $200K-$300K range.

Each property ideally has its own business bank account, as well as your master LLC.Question, is the master LLC acting as the property manager for the other properties?

Also, my insurance company said it would be the same rate regardless which option I go with.or do I stick with the cheapest option upfront like a shingle roofObviously the upfront cost/future cash flow will be hurt the most by the standing seam steal roof (although it could assist in resale value)Does anyone have experience on roofing or an opinion which is most ideal for this scenario?

Ideally you are exceeding the AirDNA numbers but it can be a good gut check on average rates/occupancy for that specific neighborhood, etc