Hiring Our First Employee!

[Shelby Pracht]

Howdy everyone! 

Our short-term rental portfolio has been growing like crazy, and I've recently had multiple people approach me about managing their short term rentals for them as well. I'm excited to try my hand at the property management, as it's something I've found I really enjoy. However, now that I'm expanding beyond managing my own personal properties, I have to start delegating!! WHERE DO I EVEN START!? 

I know we will need to hire a cleaner or maybe two, as we'll need probably 30+ hours a week of cleaning done. Should I be paying someone cash now and issuing them a 1099 at the end of the year? Do I need to have an entity to be able to do that? Can I set up a DBA to pay this person and purchase good umbrella insurance, or do I need some type of LLC/other corporation?

OR...is there an article or another forum post that goes over the basics of this kind of transition from being a real estate investor to running a real estate business? No need to beat a dead horse :)

Thanks in advance!