First big snow storm in Connecticut came and went, I have a duplex in Middletown with a common driveway with my neighbor and a back parking lot. Normally a pretty quick job since the common driveway gets plowed by neighbor. My dad travels 30 minutes to the property to tend the landscape and snow removal duties but there was so much snow my upstairs tenant helped my father out. I wanted to give $30 for the assistance and the tenant offered to do the snow removal duties and landscaping duties in the future. He is a young guy and I'm weighing the risk/reward of utilizing his help. I wonder if I set up a separate contract from the lease to utilize his help, but I wonder if I kept this separate, this would decrease any liability exposure? 

For starters, I would like to word the snow removal section as something like:

"ensuring walkways, front stairs, sidewalks, driveway, etc. be free of snow and ice after 24 hours of any weather-related event, including putting down de-icing salts on ice or icicle removal as needed'.  $30 per snow/ice removal incident for anything substantial (ice events or snowfall over ~2", lasting over 24 hours) and id reimburse for de-icers or equipment as needed."

Thoughts on the language? Not sure on landscaping yet. As an alternative, do you go with a $50-$60 per incident snow removal/landscaping professional person (with insurance) however it is a pretty small area to remove snow. Your help would be useful! Thanks.

@Christopher Kolasa I would politely thank him again for removing the snow and tell him that it is something your father really likes to do so he will be continuing to do it.

If the tenant loses interest down the line it could put you in a real bind and even more so if he doesn’t do a trustworthy and thorough job like you know your dad will do. 

@Michael Noto what about just for this winter? Issue with my dad is the distance.

If your dad doesn’t want to do it then that is a completely different story. Let the tenant do it and have your dad as a backup. Just be prepared for the tenant to let you down because that is the most likely scenario. Have a backup.  

I'm a hard pass on letting tenants do snow removal @Christopher Kolasa . What happens when they stay too late at their friends house and don't wake up at the property to clear the snow for other tenants? What happens when they go on vacation? What about if they get sick, do they have a backup? 

There's just too many variable that a tenant won't have planned for that a snow contractor should have planned for. 

None of this is even mentioning the potential liability issues here. Does the tenant carry insurance for a slip and fall claim? Who bears the responsibility for not having the driveway cleared (hint: it's you). 

I don't include snow removal as a part of my lease so I may be speaking out of turn here but I do think this is worth exploring....  Like @Filipe Pereira said, obviously you'll have some more liability here but honestly if there was a slip & fall with an insured contractor doing the plowing you still may be partially liable as well...  

What's the harm in doing a test run with the tenant & keeping your dad as a backup?  Like @Michael Noto said I would just prepare for the worst & keep your dad on standby.  It may require more communication before & after the storms with the tenant opposed to your dad, but if it saves you & your family time and money I personally would consider it.  

If the tenant does well after 2-3 storms, then maybe a formal arrangement makes sense?  

@Ryan Allison @felipe Pereira good points. The slip and fall liability is worrisome but sounds like a liability with any property. I think I'll try it out with the tenant on a temporary basis, gonna go with a test run and not guarantee anything! Seems like risk with anything but may be a cost effective/practical arrangement.

Thanks for the point of views.