@David Pulley  CAREFUL. 

Absolutely devastating to see how much destruction it's caused to Asheville and surrounding mountain communities.One thing I will say for certain, communities down here really know how to take care of each other.

If you find yourself saying "I am new to real estate", then you do need some time to educate yourself (BiggerPockets is great for that) and plan your first investment carefully before jumping in.Remember, buying a traditional rental is one of many different ways you can enter REI world.

But we also had fantastic tenants and they took care of a lot of small issues. 

People who think they can cancel the last four days only care about themselves.

After talking to two realtors with intimate knowledge of the area, we learned that STR rents and annual occupancy are just too low to even cover the PITI of properties in the area, let alone maintenance, supplies, lawn care, snow removal, etc.

I need to create some kind of significant revenue stream to ensure my wife, kids, and grandchildren are taken care of when I’m gone.

.- My mentor recommended that I sell both properties and put the funds to work elsewhere, potentially in more lucrative opportunities.I feel like holding onto the negative cashflow is limiting my growth potential, but I'm trying to weigh the options carefully.

During that time I would save and look for a house hack, might be a year or two down the road but you are 21 so who cares. 

I don't know, but your guy who is self insuring with those numbers is either stupid, nuts, or so filthy rich he doesn't care about taking losses.