Recurring work is scheduled against the season it protects against, not against whenever someone happens to remember it.
An illustrative cadence. Your calendar reflects your systems, your equipment ages, and what the property actually needs.
Feb to Mar
Before the thaw
Meltwater arrives faster than the ground can take it.
Apr to May
Opening up
The first warm weeks are the only cheap time to fix drainage.
Jun to Aug
Systems and safety
Equipment runs hardest when a failure is least convenient.
Sep to Nov
Closing down
Exterior work not done before the freeze waits until spring.