Don't we all!
Well no one can tell you where to find a Pygmy-Owl on Cypress at this time of year. I have the best success in the mountains in October when the young are dispersing to find their own territories. On Cypress some good spots to check are all along the road up, the picnic area, Yew Lake and Bowen lookout trail. Yew lake and Bowen Lookout are not open to people who rent snowshoes from cypress and are in the Nordic ski area. But they are good places to try later in the year (fall).
If you go now you need to rent snowshoes and when you rent snowshoes you must stay on designated trails. It's 26$ for the rental and pass. Don't go with the hope of seeing a Pygmy-Owl though because it's far from guarantee ranteed. Most likely you will just see Gray Jays and Ravens etc. Most Pygmy-Owls move to lower elevations as hunting in the snow is not as easy but they are found in the local mountains all year long including winter where they mostly eat hoarded food.
When you go on a hike like that you need a first aid kit, waterproof and warm snow clothes, snow boots, toque, emergency blanket, whistle, flashlight, and you should have a cell phone with extra battery charger and let someone know where you are going. Also tell the people at cypress when you rent (especially when travelling alone) just let them know what trail you plan to go on etc.
Take lots of water and snacks as well like granola bars and trail mix. At this time of year bears aren't a concern. Bring plenty of nuts to feed the gray Jays. You can have gorgeous views of Vancouver from the trails and it's gonna be a great day regardless. Listen for small birds that may be mobbing a Pygmy-Owl. Listen also for a Pygmy-Owl call. These are tiny owls, check trees thoroughly you may walk right under or by one without even knowing it.
Good luck! You will see one before you know it. Usually you see one when you least expect it. For instance last October the kids and I were hiking in Whistler and were feeding the Gray Jays, when a Pygmy-Owl flew right in and perched in front of us to check out if the Gray Jays were a good meal or not. It was pretty cool. The fun part is finding your own Pygmy-Owl. If you are in the mountains enough, in places like Manning Park to Vancouver Coastal Mtns and the Interior, you will find one. They really aren't as hard to find as you may think.
Due to past problems with too many people descending on certain Pygmy-Owls in the Lower Mainland and Fraser Valley, where some people came back daily to the same owls for hours on end and some crowds of people got too close, flashed owls and prevented their hunting, giving out exact locations is discouraged. They are also a blue listed species in BC. So if you do find one it is best to keep its location to yourself for the sake of the owl. However, if you come across one on your own in the mountains while hiking and take a few photos and move on, that isn't any pressure to a diurnal owl like this. They do seem to tolerate humans pretty well.