I would take the time to clarify expectations in writing and also to make an agreement for what you all believe should happen if for any reason he is unwilling or unable to fulfill this function in the future. 

Appreciation is largely a function of time.

While some of these buildings fails in high winds and huge snowloads, that's more of a function of engineering.

I would venture your best preparation for this type of venture is to actually work at one and gain insight to how they function.

I'll admit I'm in the anti-condo investing school.

If your tenants aren't very smart, odds are they won't understand how to use the smart technology, particularly when it's not functioning properly.Technology does some really neat things, but it can also cause some really big problems.

Some brokerages want you to work in the office and function more as a full-time agent, and some are perfectly happy to let you do your own thing.

JPMC is projecting an end to the virus over the next 60 days.

Ideally, there would be enough landlords on the site along with easy enough functionality that you could verify any landlord reference by contacting that landlord on the site.

Since it is a benefit for them, they might work with you to keep them functional.