Lawn aeration in Calgary has a fall window of roughly late August through mid-September, and the City's own guidance says not every lawn needs it. That is worth knowing before you agree to it as an annual line item.
Whether your lawn needs it

The City of Calgary's lawn care guidance is condition-based. It points to compaction, heavy use, thatch buildup and heavy clay as the reasons to aerate, rather than treating it as something every lawn requires every year.
If your lawn is thin along the paths people walk, holds water after rain, or feels hard underfoot in August, that is compaction and aeration will help. If none of that is true, you may be buying a service you do not need this year.
What clay and slope change
Calgary also warns that heavy clay is difficult to aerate and that slopes need care. Both are common here and both change the work.
Clay resists the tines, so one fast pass pulls short plugs and does very little. Slopes carry real risk of a machine getting away from an operator. If a quote for a clay lot or a sloped yard matches the quote for a flat sandy one, ask how many passes are included.
Overseeding and the watering problem
Fall is the stronger window for overseeding, and pairing it with aeration works because seed drops into the holes.
New seed needs consistent moisture for two to three weeks. If your sprinkler blowout is booked for the week after you overseed, the seed will not make it. Overseed, water it in, then winterize the system.

What to ask before you book
Is my lawn compacted, or am I paying for something I do not need this year
How many passes, and how deep
Is my soil clay, and does that change your approach
Are you overseeding at the same visit
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