Apologies in advance for the book I'm about to write but I, too, take skincare uber serious. 🙂
You have a Treat and Serum step in your routine at night; how are they different to you? Are you thinking of using a different treatment product from Serum?
What types of products are you using? I think you mentioned Canada and how cold it gets and it seems like your skin is probably combo (with the mention of oily spots); What are you trying to treat first?
What is your tone step? Is it the same morning and night? Is it an acid, or a moisturizing toner? What are you doing for eye cream?
Here are some suggestions for you based off combo skin:
Your tone can be an acid in both morning and night, but should be a different acid. For example, if you want to combat pigmentation, do a Vitamin C in the AM and a AHA/BHA at night, for exfoliation. They don't necessarily always play nice in the same application, but they do in the same day.
Don't mask everyday. It can be too much. Try to do it 2-3 times a week, and tailor it to what you need. If you need extra hydration, do a hydration mask 1-2 times a week, and if you need purifying, clarity, do one of those 1 time a week. Dependent on what is more important, you can switch the intervals (2x Purifying, 1x moisture). This would include any sleeping mask you want to do. For moisture, I like the SK II Masks. They also double the day you use them as a serum. First Aid Beauty also has an Oatmeal based mask that provides nice hydration too. For Purifying, my ride or die is Tata Harper Purifying mask. I love it. For me, I like it layered on an exfoliating mask; I will use Tata Harper Resurfacing mask for that. With this cocktail, I'm killing multiple birds with the same two stones: I exfoliate (tone), address pigmentation (also tone), deep clean (purify) and moisturize (Tone too). I do this once a week. On days where you mask, be aware of what other products you use. If your mask is specific for hydration, be careful with how many hydration products you use. SImiliarly, if your mask is for exfoliation, do not exfoliate again that day.
Implement an eye cream; 2x a day. Our eyes can age us really quickly and while no eye cream is going to reverse what is happening, or fix hereditary stuff, it can help treat, temporarily the signs. Also, eye masks are a great option for lines, wrinkles and darkness. I like the Shieseido Retinol Eye Patches for a mask option. I do it once a week. For eye cream, one with retinol, which can help with darkness may work for you. Dr. Dennis Gross has a Ferulic one, and Trish McEvoy has a Retinol eye cream that I've used for years.
Use a good moisturizer. I have had dry skin mostly and I see a huge difference when I started to moisturize properly. I switched to oils for moisture and I try to be aware of ingredients when thinking of moisturizer. I use nothing with alcohol because that is drying. There are lots of night oils on the market; Aurelia Cell Renew Night Oil is my oil of choice for evening. I have also used Sarah Chapman Overnight Oil. Also, Sunday Riley makes oils. I haven't used them but people around BIC love the brand. You can also incorporate an essence, or spray to help with moisture. Fresh Rose Spray is a good one. Herbivore also makes so great ones.
Hope this helps.