I imagine this would take close to a year if all went well, and eat up a lot of funds.

I could not imagine running a STR myself or even getting it started.

I imagine I am making rookie mistakes but am learning as I go. 

I'm also curious about creative ways to finance the project as its hard for me to imagine a bank loaning me this amount of money.Thank you for any input and questions. 

Personally I wouldn't use Zillow, I can only imagine they want to introduce a future fee for the service.

I am also interested in finding such events in Lancaster County and have found this to be much more daunting than I imagined.

Your market may have something to do with it also.....in the San Francisco Bay Area many people will NOT get a 50% rule....I would imagine in Miami it's the same thing....however....if you are investing in certain areas of the midwest .....Ohio, Tennessee, Missouri or Wisconson....50% rule should definitely be a deal breaker because if your property does not meet it....then move on.

I can't imagine a cleaning company agreeing to a different cleaner every time.

I would imagine just to make something like this pencil, the cap must be pretty high, right? 

@Aaron Mazzrillo, Hotel income, as you may imagine, is highly cyclical.