Currently, I have an LLC that operates as a management company, which collects all the income from my two short-term rental properties.

I served as the buyer's agent and property manager for my clients under Blue Chariot Realty & Management.

I am a CT based investor, flipper and property management company owner.  

Kirk Hey Kirk, nope we are property managers.

And will you be utilizing property management firms to help out? 

But even being a Landlord and outsourcing that staffing via Property Management still requires someone to manage the managers. 

Even if you break even, you will lose money every month it sits vacant, when you need repairs, property management, etc.

Next question.... will you self-manage it, or turn it over to a professional management company, or some type of hybrid? 

Quote from @Josh Jung: surprised you haven't heard of RBP. it's like a mix of services you can offer to your tenants like renters insurance, virtual concierge, etc So the property manager/landlord pays for their renters insurance, and filters?  

One reason was the condo management company wasn't doing a great job and there were always extra levies.