You are a high w2 earner, The house is worth 110k today, you are buying from your grandma for 60k in exchange for free rent for life, upside ARV of 200k.The costs of owning the house will help provide tax relief on your high w2 earnings, you are buying a great chunk of equity that will pay off in the future, and you and your grandma are doing each other solids. 

Especially when there was far wealthier people than me spectating my journey, and probably highly successful and well to do  people here reading this. 

I've been a real estate investor my entire life, doing my first deal as a senior in high school ($5,000 mobile home).

Even though the nightly rate is high, the RE has such high value that the margins are fairly tight.  

We decided the cost was too high and it was not worth it from a financial or risk perspective.  

However, if you're a W2 high income earner or business owner, I can't imagine it makes any sense to flip houses, mail mass post cards, wholesale, or build lead gen websites with the value of your time being better spent other places (such as learning about real estate and increasing your income through proven means), such as at your 9-5pm or growing your business, and your real estate is a long term process and you don't need "home run" deals to qualify or make it work.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Or for the high-end primary homeowner has no legal way to 1031 exchange; so the deferred sales trust is a no brainer.

How bad is the insurance, how high are the property taxes, is there an Hoa, etc etc. 

These are prime locations, think near downtown or popular tourist destinations where demand for short-term rentals is typically high.