We will be a licensed brokerage.

Just a final thought I'm not sure actually fits in here but wanted to say: I have my real estate license.

Now if you're able to do new construction and pull out all your money except 5%, you can scale much faster.I'm building in eastern tennessee and recently got a GC license. 

If you operate an STR, gross income is your total rent paid by your guests, before any subtractions.To figure out your taxes, you take this gross income and subtract from it all allowable business expenses: marketing, education, technology, licenses and fees (including Airbnb and credit card fees), office expenses, business driving and so on.

Licensed brokers can help with qualification, as its a very simple process, and get you your fifth property.

My intention is to live in the basement, rent out the remaining bedroom to a long term roommate, and run the upstairs as a full time STR.I'm aware that the City of Littleton has strict short term rental regulations, but they do allow STRs as long as I have a license and I am occupying the property.  

The real estate license isn't magic.

I’m also a licensed general contractor.Thanks in advance!

And a few who do real, sustainable business.For an industry that loves to hate on agents, it's remarkable how most of them earn less, and do nothing compared to their peerset who simply get licensed. 

We are allowing her to find someone to replace it and save money as long as they are licensed and we approve it.