Experience or Reputation && Why?

You can't forget building a reputation with your own direct booking website and bookings.com, Mariott, etc.

I like your attention to water and moisture - its one of the leading causes for property damage.  

This presence alone has drawn other logistics and distribution companies to set up shop in the area, solidifying Louisville’s reputation as a key logistics center in the U.S.Moreover, the automotive industry is making waves with Ford’s massive investment in the BlueOval SK Battery Park in nearby Glendale, Kentucky.

Not having the correct team and systems in place and totally damage your reputation as a property owner/manager, if your team (the maintenance company) does not have the same vision as you.Perhaps there is someone out there and if so . . .

Perhaps, your PMC needs a better lease or an addendum to cover issues like this.PMC should send a warning letter that clearly outlines repurcussions of what will happen if the tenant doens't comply.YOU must be prepared for the tenant not paying, requiring eviction and any potential retaliation damage to the property.

He lives a standard young professional life, so no damage or issues have come up in the past 3 years that could break any lease terms. 

The roof rafters are falling due to water damage.

Below is a picture from a tornado that hit one of our properties and another of a fire claim we had a year later.I'd look to find a reputable roofer that has experience with insurance claims.

(biggerpockets.com)When assets are damaged: How a cost seg study helps if an asset gets damaged!