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.

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.

However, I am worried about the daily maintenance cost of it and would like to understand how others have gotten comfortable. 

As @Linda Weygant weighed out, a rental should not be subject to SE taxes unless it is short-term and substantial "hotel like" services are rendered -- e.g. daily maid services, continental breakfast, shuttles, laundry, etc.Your flips should be in a separate LLC. 

Did you slide your debit card at the "Sweet Green Relief". buying Starbucks daily?