If it's helpful and we can measure a business impact, we will scale.

For example, they have not sent us the rent they owned us for the last three months, and here is paperwork to show it is not in our account, here is the contract with them stating they would pay on this day each month, and here is the title of the house in my LLC/name to show you we own the property too.

They pay you rent, and they operate a parking business.

I normally advise that people start a business as a sole propeitor in their first year.If it is successful and something you want to continue, then have a conversation regarding entities.

Maybe I could leverage my other business but I don’t know the requirements for that as we do have outstanding loans already 

Quote from @Don Bessette: First, you need to realize this is a business relationship.

I am looking to buy my first investment property and have seen strong fundamentals in Indianapolis (job growth, population and median wage).As an out of state investor, I am looking to connect with investors/agents in the area to build further knowledge on specifics with the markets and hopefully bring business to in the future!

TurboTax has rental property features, and the IRS has a great guide on rental income, deductions, and recordkeeping - IRS Rental Property Tax Guide.https://www.irs.gov/businesses/small-businesses-self-employed/tips-on-rental-real-estate-income-deductions-and-recordkeeping2.

My biggest piece of advice is to run it like a business especially with the tenant next door.

This is a time consuming business.