I read the tax regs and read it to say that if the property was not maintained and went into disrepair and you had to replace the "deck" you had to depreciate.

Some choose to maintain.

Nothing in this section relieves either the landlord or the tenant from their obligations to maintain the dwelling as those obligations are set forth in Article 2 and Article 3 of Chapter 12 of Title 55.1.e.

For example, investors strictly looking for cash flow may not maintain the property at the same level as a long-term buy-and-hold investor hoping for some appreciation.Build a team you can trust. 

If a house is properly maintained and upgraded, it can stand for a long, long time.

This holds landlords accountable for maintaining their property.

Optimally, I would like to learn how to manage the rehab process remotely by myself but that seems unrealistic at his point.

The house is well maintained but there are always a few things to be done after the green card inspection but this process has been painfully slow (our inspection was Feb 2020 and we still haven't received a report).

Culture of the group - is it established & maintained?

So you'll have to do your own due diligence on what to expect for rent- the vacancy rate used in calculations will be higher than the average for Chicago; You'll have to take do some homework on the cost to maintain.