I want to add that this rental business is for vacation rentals/short-term, rather than long term rentals.

There are some good people in business, but there are also nasty, hateful people that will cut your throat for few bucks.

What insurance are you all using for furnished medium term (30 days and more) private room rentals?

Are you looking for official businesses, or more local mom-and-pop Property Managers?

We are looking for private lender recommendations, and also, can we achieve private financing inside of 30 days?

For those landlords who take security deposits in City of Chicago, is a separate business bank account sufficient for the security deposit or do I still need to set up the special landlord account that requires all W-9 paperwork from tenants etc?

I am very new on this business.

I want to start a business and I want to use that money towards it.

Nothing wrong with being a private money lender.

Or save yourself a lot of work and develop a relationship with a private money broker who can shop for you.