Quote from @Erick Pena: A "good" rental property is one that covers all expenses (mortgage, taxes, insurance, maintenance, property management fees, and any other costs) and still leave a surplus (commonly referred to as cash flow).Calculate cash flow as: Cash Flow = Rental Income − Operating Expenses − DebtThere's much more to it, but that's the basic idea.

My questions: - Looking to understand pain points of operating in Indio that you wished you had known - Besides the music festival in April, is there frequent tourism ensuring you are making the annual CoC ? 

I was conducting an extremely seasonal business and after 8 years of operation the business was insolvent. 

The properties we operate are all in Indiana. 

Hi, we are a small operator with 14 doors and Grasshopper told us we can't send texts anymore because we don't have a website.

You could form an LLC and have the operating agreement that allows your boss to require you to purchase his membership interest (or allow you to purchase his) in a given time frame.

It's the lenders who usually require that the property is listed under an entity, depending on the state that they operate on.

Currently, I am self managing all the operations.

It's important to understand the zoning/code requirements and obtain all necessary permitting if you intend on operating your real estate as STR anywhere in the country.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).