My Super and I haven't been getting along lately.  He's helps me manage a 6 family multi and he occupies one of the units with his 2 kids.  I'm trying to decide whether we should go our separate ways or if I just need to do a better job managing him.

First off, he's not a bad guy and I trust him.  He pays $1000/mo in rent, which is about $500 undermarket.  Plus I pay him $150 for basic maintenance (grass cutting 5 mo of the yr, snow shovelling walkways 3-7x a yr, light hallway cleaning, occasionally helps w/ lockouts, takes the garbages out on the correct days, etc.).

In addition, as the building Super he keeps his tools in the basement and I give him some additional storage down there. He also gets sole use of the driveway which is a perk b/c he has an F150 that would be difficult to park on the street.

I also give him extra money for additional side jobs. In the past few months he's been paid about $25-30 an hour to do some roofing and gutter work, laid down new linoleum in one of the bathrooms, porch repair, etc... 

The issue is he feels I keep asking him to do more and more (as part of regular maintenance) and I "don't treat him as an equal".  For instance, I asked him to repair a broken window and install a deadbolt just yesterday. He routinely hauls some construction garbage off the premises when it builds up (from remodeling the units). In my mind, I try to keep him busy and keep making incremental improvements at the house.

I feel that he complains and whines about things instead of simply communicating when his workload requires additional pay. I feel he's being ungrateful at times for the $650+ per/mo in benefits for typically 7-8 hours of work per month.

We've had the same issue several times in the last couple months. Do I need to manage better or is it time to go our separate ways? I certainly like having the extra eyes on the place (I live 25 mins away), but perhaps a change is in order. Or maybe I'm just a bad manager of him?

Apologies for being long-winded with this....