In both my WI 2-unit properties, I just note in leases for BOTH units that tenants are responsible for snow removal of the walkways and off street parking. 

The water company did not pay for any of the work to install the line, patch the walkway we had to dig up, or patch the lawn.

Depending on whos land it is, I wonder if you could put something non permanent down such as stepping stones or even wood walkways that you can easily remove.  

If your properties are more than a few miles apart you'll spend more time moving equipment than plowing snow, unless you get a tractor for each property.Same with a tool cat, but the tool cat can do walkways easily.

Also make sure your property line water shutoff IS NOT going to be in the middle of a proposed finished driveway/walkway etc.The run cost was about $3500 for all & the GC ate the new potable water line mistake(s).

When that permission is requested, we advise them to use a professional to install, and that they will be responsible for any damage caused by the AC due to improper installation, including creating a hazard either by protruding into a walkway, or condensate draining on a walkway creating a slipping hazard; or draining improperly, damaging interior or exterior walls or siding.

Cracked walkways, rotten steps,  etc. that you were aware of  Ask your provider.  

Say the postman says he tripped on the walkway. 

I bought the house late last year and have been watching for a four to five day window of good weather to add a concrete driveway and walkway to the home.

I also state: no smoking inside the house, late fees for rent ($50 per month), $45 fee for insufficient funds, lease automatically renews for 60 days at 125% of the rent unless landlord or tenant gives notice to terminate the agreement, overnight guests limited to 5 consecutive days, no nails and scotch tape on the walls to hang items on the wall and use of Command hooks/tape for damage free hanging, no antennas and satellite dishes shall be erected, tenants responsible for landscraping (mowing the lawn), snow removal in driveways and walkway to front door, and cleaning dryer vent.