Are you keeping the roof? Is the budget for this phase mostly for landscaping? What climate zone?

Since you have such a wide range of colors you could use - what colors are your accent tones inside?

A wider and deeper platform at the door with a solid planter box as the railing that went from basement window to basement window - if it were my house I would take it out and around the tree with a cut out for the tree so it was closer to square and solved that problem permanently. For privacy at those pbasement windows, I would still bring stairs forward.

Pine green shutters, trim at windows, flower boxes, foundation against the white would be a winner. Test bm pining for you . . . do all the stairs and treads in green, white planters as solid rail perimeter.

As much as I am a dedicated tree lover, the two evergreens that are limbed up in your front yard should go, with the stumps ground out. Wrong tree for those spots...they need to be in a big expanse, and left with limbs at the bottom as they naturally grow. They are an early mistake made by a long-ago homeowner...I'm sure they were neat looking at about 8 feet tall. Libradesigneye's ideas for the house are excellent options. A color change and a little refreshed landscaping should perk it right up.

Great feedback! I appreciate it very much - thank you.

In response to the questions:
- roof remains the same colour (it is less than 3yrs old).
- planting climate zone 5b (southern area of Ontario Canada)
- trees - yes previous owners definitely loved trees, unfortunately the cost of removing them is very prohibitive.
- accent tones inside are very dark brown/black woods for cupboards, and furniture accents. wall colours vary depending on function of the rooms but are consistently neutral tones (beige/grey/silver green) all trim is white.

- not replacing the shutters - interesting suggestion, thank you. I will try to visualize that.

changing the trim colour - was contemplating white and the entry (steps/landing) to be Trex decking in dark grey with white posts and black railing

A white house is classic, but should have contrasting trim. I pulled a color from nature without any clues about your style inside - now I visualize a very neutral comtemporary space . . black shutters are fine, but you need a pop of color at the front door., Suggest - medium / silver gray trim and a cobalt front door. Test bm cobblestone path - a bit of minerality to it - http://www.benjaminmoore.com/en-us/paint-color/cobblestonepath great with the gray trex and black shutters. Then, at the front door - bm carribean azure http://www.benjaminmoore.com/en-us/paint-color/caribbeanazure

Hope you'll consider the stainless cable horizontal rails - you can use wood posts - see also the neat modern detail of horizontal spaced lattice for under the deck - very nicely done.

Those trees aren't going anywhere in BC - they are huorn like - will outlive the house. Embrace them at the deck (and get a dremel saw so you can scribe to them/ adjust the deck opening as needed). May I suggest you rework the house number over the garage - something bigger and a modern font number there would be great - you can get those online in black - 6" high -take down the cottage sign unless it was yours.
I'm not a big fan of the busy look of your existing storm doors but I'm sure the winters require a strong option. Paint the entry storm door the same color as the front door. Paint the secondary storm door and door behind the trim color so it recedes. New larger light fixtures - and for summer, why not string party lights from the trees to the front door - when you redo the deck, get some exterior outlets set on the front facade - you may be able to have a party in the front yard with the right entry deck (or at least a couple of beers with a friend after hunting)

There are some industrial lights popular now that come off the face of the house a bit - black or gray - this is a kind of cottage interpretation that isn't too industrial but adds that sense - http://www.lightingdirect.com/trans-globe-lighting-4775-single-light-down-lighting-outdoor-wall-sconce-from-the-outdoor-collection/p723589

Four months later we have made a few changes

That looks very nice, kelst! What a difference!

Great decisions made as it looks just awesome!!!

kelst - congrats on the changes. Looks great. I have a bungalow and similarly looking to replace the entryway (concrete steps up to front door). Any details on your new entryway would be appreciated (materials etc.). I'm in Ontario as well so need to make it winter friendly.

picture attached

any front landscaping tips would also be greatly appreciated - want to make the front of the house less bare

First remove spruce and bring a walk way maybe with a couple of steps down beyond the rear for where the car is parked

Some current photos showing the whole front of the house with the new changes and the view walking up the driveway would be helpful in suggesting new landscaping.

thanks for the tips. I've attached two more photos which provide different angles of the front yard. I haven't changed anything yet - this is how the house looked when I bought it. Appreciate any advice or suggestions.

Matt, start your own dilemma. You will get more attention. Right now we are focused on the OP.

kelst, love the front steps...with the landing which breaks up the former steep look.

Since the siding is white, I believe the white foundation will look wonderful and will be a good background for any foundation plant you choose. I love the blue shutters, but I can understand why you would want shutters that match the dark grey roof and why you would want white on the trim around the roof edge. Perhaps you could paint the door this blue color. I believe evergreens and red-leafed plants will enhance the white and dark grey color scheme very well. You might mark the path to the door by putting large pots of plants along the walkway, from the driveway to the porch rail. In fact, if you like the blue, you might paint wooden flower boxes and terra cotta pots this same blue to point the way. Your home basically is a very nice design that has a lot of potential.