Property Value: The DIY option is viable for properties with improvements under $1.2 million improvement value (acquisition cost minus land allocation), covering most 1-4 unit dwellings.

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

Then I have standard 12-month lease that covers me and my condo appropriately. 

Our rent covers our mortgage plus a couple hundred. 

Once you have the establishment of the 2 year owner occupancy that's help you to cover the capital gains portion.

No 20% down needed, just the closing as long as loan amount covers the current payoff.

I find smaller, more boutique managers often do the best job; they know the nuances of the market, and they can eek enough out of your property to cover their salary vs if you did it yourself. 

We subscribe to a home warranty that covers most repairs for $360/ yr.

If they have renters insurance it may cover their cost - that will have to be figured out.

Your conversation(s) should be with your PM, not the tenant.They may need to screen better.They may need to take more effective action and sooner.Travis hit the nail on the head - another phone call from someone won't get tenants to pay faster.