Check out this Berkadia 2021 Forecast.

I believe the majority of my time will be spent:Analyzing the property to acquire and forecasting cash flowThe actual acquisition process with related partiesDeveloping a state-specific lease, and one in line with our leasing model.Leasing the officesMaintenance (although the offices have an HOA)I assumed that the aforementioned activities would all fall under the bailiwick of a property manager, although I do not have in-depth experience in this field, so I may be looking at it simplistically.  

Your weather is fairly similiar to ours here in central Texas.

How long are people going to still want to live there when they can make the same money in places with much cheaper real estate, rets, cost of living, much better weather and much less stress?  

Also check the main door weather strips, make sure there are no drafts. 

Covid is a great example of how we cannot prepare for every variable that could come our way, but if you are invested in the right asset class that can weather the storm, you will be able to sleep at night.

lol  But seems like you know what has to be done (20+ years on a regular shingle roof is good), so find a reliable roofing contractor in your area, work out a deal and get it done in about 1 month (weather permitting), and things fall in place.If you have specific Roofing questions, let me know!

Pretty much every city in the U.S. has some kind of weather issue.

Some markets are forecasted to increase at that rate over the coming quarters--this is why people are buying at such low cap rates, even with the threat that cap rates decompress somewhat.Eventually someone is going to lose this bet. 

Even with a downturn because of principal paydown the asset has strong capability to weather multiple market environments.