The more knowledge you have the better equipped you will be in vetting a partner.  

From an Insurance Agent's standpoint, the AC work will not be covered unless you pay for an endorsement such as equipment breakdown (similar to a home warranty).The claim to reimburse the tenants for their time spent in a hotel may or may not be payable based on your insurance policy. 

I still send them reminders tho.Fees:  This one is tough because you have an aging and depreciating equipment. 

I hired them because they project manager who oversaw the rehab at the properties was not equipped or experienced in property management. 

You will have to JUMP at some point but equip yourself with adequate tools for the tool belt.  

However, you can equip yourself to answer those questions.

Is it OK that the equipment and pump shed is unsightly?

He is on site and has the equipment.  

We work with our investors buying properties and look for properties that have "other" opportunities increasing revenues from a variety of means , vending, rubs, bulk savings, extra services.  

My concern is of course the expense of replacing/maintaining broken equipment.