It's also really cold outside as well, which he mentioned that "we don't want anyone dying of exposure". 

As professional PMs, these scenarios are less anxiety inducing to us because, unfortunately, we deal with professional tenants more than your average landlord.

The ONLY reason why it looks like SEO is competing for that minuscule amount is because SEO is the only strategy that GETS/TARGETS that minuscule amount (which is what you want).When you send out DMM cold calling and texting, you are targeting the entire population so you THINK you have a large audience, but no no NO!

Some properties there's just a Brita water pitcher the cleaners fill, others it could be bottled water cold in the fridge, and others would provide nothing because in all reality guests bring the drinks they want.

The cold truth is no one cares.

It is possible, but you have to put in the work; driving for dollars, mailer campaigns, cold calling, building lists, etc.  

Cold calling

I would like to buy a future retirement home to get away from the cold winters but in the meantime would love to rent it out as a vacation rental.What are the good areas to consider and where would I get the most vacation renters and cash flow?

Bandit signs, cold calls/texting along with direct mail is the method most people use.

I have a bit of anxiety when it comes to meet ups/networking, so I have a difficult time convincing myself to go, but I am working on overcoming this weakness.