Consider adding amenities like beach gear or a hot tub to boost bookings.

To answer your question I would highly recommend shopping around on the BP online bookstore and finding a couple of books that stand out to you.

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.

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.

Everyone's favorite answer in real estate---"it depends".That being said, you have to start somewhere to figure that out.

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

Quote from @Lawrence Mitchell: I've read a few books on real estate and something the majority of them had in common was the BP community so I would like to see what it has to offerHey @Lawrence Mitchell, welcome to the BP Forum!

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. 

I am currently reading books and educating myself about private lending.