The odds of hitting red are 47.4%.

Or the kitchen cabinets bright red?

Its since sold and whomever is rehabbing it is making it look really nice, but I seriously wonder WTF was going on in that one "dark red" bedroom, like there was a cigarette smoking competition going on for the last 10 years. 

If this coach is in your market and knows the key players in the market, has used various property managers and can tell you the good ones, knows the loan brokers, knows the risks of investing on this side of town versus that, knows the tenant base for your area and what they are wanting from their apartments and what they can afford, than I would say a coach (maybe not the one you are interviewing) is worth it.  

That's the red flag for me.

What are some red flags to watch for when interviewing Property Managers?

As for your negative cash flow situation, being in the red 900/month is not a good place to be in, especially considering an emergency can happen at any time.

This is one regional player, one statewide, and one national.The price of answers to "but what about if..." is a phone call.

Be suspicious of these red flags: any last minute changes just before closing, anything sent via email, anyone insisting on using their own title company or notary, any title company or notary that your closer/agent hasn't used before.

Probably need a track record, probably need 30-50% down equity to be a player.