I think making it more generic and less custom is the safer bet.

If you tie the bonus to early renewals, a bad employee will renew bad tenants just to earn a quick buck.

Quickly I learned I knew nothing about the business of trucking and truly didn't enjoy it, as all those gains got depleted.

As you said, this allows you to track LLCs (locations) and properties (classes and/or customers).

After months of reassemble and some customization work, the property sold for a decent profit.

If you present the listing well, put it on multiple platforms and are asking a reasonable rent you will get plenty of interest and applications quickly. 

Quote from @Don Bessette: I have a 30 plus year tenant that can not keep up with maintaining their unit, it is filthy inside and in desperate need of renovation, all systems are in good repair and I respond very quickly when issues are brought to my attention.It is also well below market rent, and they struggle to pay the current rate.Looking for suggestions on how to gently proceed with the notification to move. 

If things go sideways, you discovery greater rehab expenses, the market takes a turn for the worse, you can get in the red quickly. 

As there is a general flight to affordability, the new developments don't fill as quickly, and rely on concessions and/or lower asking rents to fill up.  

I know out here on the West coast with our digitalized title plants that each title company has it would be a matter of a few clicks for customer service department to transmit a copy of the mortgage to me..