Unless you have an STR-friendly HOA in a tourist hotspot (Honolulu, Las Vegas, etc...), I personally don't like properties with HOAs if your plan is to run them as STRs.  

I have two friends who own rental properties and they are successful with their properties, I read Rich Dad Poor Dad twice along with Rental Property Investing and Power of Habit, I've been told by multiple people apart of the Baby Boomer and Generation X that they wish they invested in Real Estate at my age, I was a Resident Advisor at my University and I enjoyed that role so some of the skills are transferrable, and lastly this is the best time for me to take a risk.

You become a mark.Constructive criticism is your friend.

The first line you mention the increasing friend of investor looking for.

I felt that it was very well done, covered a significant amount of material, had a friendly and motivational feel, and was a good experience and a worthwhile value for $1500.

I have friends who own properties with 5+ units who Airbnb 1-2 units in those buildings but again there are limits to the scalability thing. 

One of my friends recently asked me for advice, and I want to make sure there's not something I'm missing or a better option for him. 

Nature is not friendly, he said: it's either polar winter up there or you can't breath because of the smoke.

I have friends that routinely complain about it.

The impact on real estate is twofold: increased demand for housing in both the rental and purchase markets, and a shift in housing preferences towards urban, tech-friendly developments with smart home features and high-speed internet connectivity.Relative AffordabilityWhile many markets are pricing out investors, San Antonio is maintaining its reputation for affordability.