Grass not mowed for months in the winter time

Hello, I have a property that’s a couple hours drive away so I am not able to stop by and check as much as I like. I have a situation where the lawn was not mowed for several months due to it being the winter time and grass not being long enough. The property manager has heard from the tenant that the grass needs to be mowed. Not sure if we should keep having to check with the tenant if the grass needs to be mowed but I also understand that it can be unpredictable when to mow the grass in the wintertime. Has anyone ran into this situation and what type of systems have you or property manager come up with to handle this? We have a regular 2 week schedule during summer and spring months so this issue is specifically occurring in the winter only. Thank you.