My Name is Miles, currently living in Arlington (DFW Area), I've always had intentions of at some point getting into real estate, now at 40, and finally at a place financially that it is feasible, I'm planning on spending the next 6-8 months learning all I can (and then rest of my life continuing learning lol) before taking the FIRST plunge.

I have one rental property now that was our old primary residence that is finally cash flowing and I have about $100,000 equity in that property.

Been through a few book keepers who don't seem to understand this space very well.  

The trade off course for STR route is more management/cleaning of guests coming and going/risk of no bookings vs not needing to deal with long term renters months at a time if that once they move in.

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

Our goal is to have a small but mighty portfolio, much like Chad Carson’s model he describes in his book and podcast.

The book on rental property investing : Brandon Turner

Things like touch-up paint, minor trim fixes, and final deep cleaning can often be done while showing the property.

. - You will finally get a tenant. 

A lot of the cost is associated with the drive to get out and back to our lake house.If your friend isn't listed on VRBO, she is missing out on revenue and bookings.