I now work in a coporate setting and on a daily basis I cannot conceive how others can sit behind their computers for 8, 9 or 10 hours and not be utterly stricken in the soul of how this is not how we were meant to live our lives.

Your business model is not unique and given the fact that you are a recent graduate I doubt you have much capital.The arbitrage between yearly rentals and weekly/daily rentals provides some upside, but the profits margin is slim and you are going to need to find buildings that allow short term rentals.

Serving as my daily dose of motivation and inspiration, I drive by  brand new Lamborghini, Lotus, Ferrari, Alfa Romeo, Porsche, Maserati, Mercedes and BMW dealerships.

Selling my personal house...there was a crawl space moisture issue that has been 100% repaired.

Thank you guys, I am reading up on stuff daily.

@Frank Wolteri would not sell a single one. i would delegate the daily operations to a management team. 

You can use sites like Airdna.co or Everbooked.com to research occupancy and daily rates but also just look at other local listings to get an idea of rates and how much they are booking.  

And I need to be reminded almost daily to KISS!

I have definitely considered house hacking and I check Redfin daily for multi family properties here in SD but the same issue with affordability comes into play.

Since it won't be in the bedroom dealing with moisture - would I need to vent it outside or would venting it to the attic space or right underneath the roof vent be sufficient?