I've worked with several loan servicers, and no matter who you use, it's not fun setting it up, but I've had easier success communicating with OnePoint.They have a login portal to track payments etc, like you mentioned. 

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

These areas are relatively easy as a direct flight from SFO and one of the BP videos mentioned how it's a good idea to be able to fly direct if you have a OOS investment.

If there are lease violations, mention them-you not having a key to access the unit WITH proper notice or in case of emergency is one of them.I'd also tell the tenant that they are clearly not happy there, so finding a new place is in their best interest as well and as they have several months, they should have lots of options.

The other info sounds great but I would verify the assumptions I mentioned because if they’re off, it throws everything else off.  

@Mark Lee this is a team that I have used multiple times and like it was mentioned, they don't have to be anywhere near you.

@Tamika Davis One of the biggest advantages of most software on the market is to complete these tasks you mention (maintenance, leases, rent collection, etc). 

Like @Jesse Rivera mentioned above, I also go to a few sessions but spend most of my time in the lobby or at the bar making connections."

@Benjamin Bieber   I have heard of the company you mention but know nothing specific about them at all, but anytime you buy a property you should do your OWN due diligence.

There will not be one PM covering all the places you mention in your post, so maybe refine your search a little, and then you can start interviewing.