For all you know their "six months is all we need" is based on what the insurance company policy-limits are.On the other hand; maybe the house is 20 miles away.

As I grow, I can then set up other LLCs to keep key properties separate, or segregate my rentals once I own 10 or so in a specific LLC.Having the manager being the managing partner across all LLCs will allow me to have one single checking account to manage all of my rentals no matter how many LLCs (elected as partnerships) that I eventually have.From an insurance perspective, I Just plan to have an umbrella policy for each LLC and individual property insurance on each property.All good so far (I think).

My personal experience with a number of rental properties and the advice of my attorney was to simply get a good umbrella policy ($500 per year for a $2M policy).

You will have to ensure your insurance knows it is vacant and the policy will be more expensive when it is vacant.The other question I have is, you used to live in Chicago, how long ago was that?

If you're worried about liability just make sure to have a large umbrella policy.

The following is the standard late fee policy listed by myhomespot.com.

Others have their own internal policy and limits.

If your tenant does not pay, you must cover the entire mortgage on your own now - If your evecting, this may continue for several months - with a duplex, at least you would have another rent check to fall back on.Also, when you consider taxes and insurance - it would cost more in taxes if you purchased two homes and paid for two insurance polices Vs paying taxes on one property and only one policy.

@David L.Your landlord's policy will cover rebuilding it but will not cover the tenants "stuff".

As far as insurance, the short term rental insurance is one of the most expensive insurance policies you can buy.