There's secondary trend also that mimic like you said, most happened due to baby boomer generation, they keep moving up house but then when retirement age is near, they purchased outside the  area, so lets say they purchase SF in Daly City,CA twenty years ago for 300k , now they sell their house for 1.5M ; when they have no job or near retirement, they move to Sacramento where home price is still 400k-500k.

I spoke to several locals and they said as much as they love living in Aspen the overall cost of living is just really high because everything is expensive... gas, food, clothes, taxes, utilities, service work... so I would imagine that owning a rental would come with a lot of higher than usual upkeep costs as well.

Guys and ladies who work hard, live below his or her means, and stack cash, either waiting to reinvest, are currently buying, or are busy working on properties.The issue I do have with the financial freedom people are when they show airplanes, luxury cars and people dressed up and wearing designer sunglasses in their ads, when they should be showing a dude wearing work boots and dirty clothes standing in front of their pickup truck or work van. 

What would make baby boomers and the silent generation vacate their homes?

I pay support and still pay their insurance (medical, dental, vision), clothes,  school snacks, and am the only one that takes them on vacations.

I still feel like a baby in the woods when it comes to ways to borrow money.

There are ways to get out of it early but only as a result of your life circumstances changing (like having a baby and needing more space, moving closer to your job, etc.) 

The Inspection report reveals Cloth Wiring in the house (apparently only one insurance company insured this type of wiring issue in Florida due to fire hazards), also one GFI in the entire house, almost 30 windows needs replacement (all shut) . 

LANDLORD is not liable to TENANT, guest, or occupant for personal injury, damage to or loss of personal property (furniture, jewelry, clothing, etc.) from fire, flood, water leaks, rain, hail, smoke, ice, explosions, interruptions of utilities, criminal conduct including theft, burglary, assault, vandalism or other crimes, acts of God, or other causes unless caused by LANDLORD’s negligence.

😛 All joking aside, congrats to everyone - I "know" most of those people on the list and with the exception of Nathan they're all pretty good guys 😛😛 (j/k Nathan's my brudda by anudda mudda, we're even both baby bald) 😛