Hello Craig,
Having entered the STR market in 2014, I never thought a Pandemic would wreak such havoc. The travel industry is change as @Ken Latchers has eluded to. If I had to do it all over again I would consider the following:
Top 10 Lessons Learned: 1)Location is still everything. 2)Vacation Locations are more susceptible to significant upswings and downturns. 3)Transportation methods are an important consideration 4)No matter what, DO NOT trust ANY of the "current" OTA's (Airbnb, VRBO, etc), they are NOT looking out for your best interests 5)Whether or not you use a management company, prepare to spend more time dealing with them than you initially anticipated, so you might as well self-manage, and it is "doable". 6)View the properties as inventory, not "homes" and be prepared to pivot quickly. 7)Define "guests" for yourself. I define them as people I would welcome into my own home; people staying in my STR's are travelers - this helps me keep things in perspective 8)Travelers will treat your STR's like any other hotel and will ignore many of your rules 9)Treat it like a business, not a hobby 10)Your cleaners are your lifeline, find ones you can trust, pay them well, and they will help you enough to replace a management company.
It has been good, lucrative and outperformed any other investment. Best of luck!
Mike