This included modernizing the kitchen with high-end appliances, upgrading bathrooms with spa-like features, and adding hardwood floors for a luxury feel Lessons learned?

You don't know for sure exactly what their occupancy rates are but you can certainly get a feel for it by seeing what future dates are open.

Feel free to reach out with your scenario details.

Additionally, it feels the most appropriate approach for both profiles I described above and allows me to focus on learning one strategy.

If it's a larger organization, feel free to inquire about their different staff qualifications.2.

Use AirDNA to get a better feel for what may be projected and then dive into Airbnb and compare to your competitors. 

I like using these for just this case.Another item to consider is since this is a 2nd floor I wouldn't be that worried since the 1st floor will heat the 2nd floor enough to not allow frozen pipes.I would also talk to an HVAC person because I believe they can also put a device to cycle the heat a few times a day or even put a secondary thermostat in the apt to take care of the minimum issues.I feel for you because otherwise you have a great tenant.

Just getting a feel for things. 

I feel quite intimidated only seeing people with large followings and MULTIPLE properties.

Still, my soft heart left my head feeling pretty rough, like a "failure".I don't think with your experience and 17(!)