Before I start talking about this room, I'd like to talk a little bit about the challenges inherent in my house. A standard Chicago city lot is 25' wide by 150' long. Houses tend to be long and narrow -- the house is roughly 18 foot wide as there must be 3' on either side of the house. Our house is on a road that runs east-west, so the long dimension of the house runs north-south. We're on the south side of the street, and our best light comes into the south side of the house.
Our main floor is composed of only two main rooms, the living room area takes roughly the front half of the house, while the kitchen, dining, family area comprises the other half. The ceilings are tall in both rooms. I think they are 10' in the front part of the house and 12 in the back part, since there is a step down from the front to the back level.
The play area is essentially part of the back area of the first floor.

This is the view of the western half of the room where Z's play area is located. There's a fireplace at one end and the sliding glass door out onto our deck. The floors are all hardwoods and all the walls are still (sadly) white.
This is the same half of the room, only facing north (the rocking chair is for reference). The door is to a small pantry. The window faces onto the deck of the apartment building next door and we don't get much light through it.
This is a better view of the toy storage. We are using an Ikea storage system because it is relatively inexpensive, flexible and the bins are cheap to replace. And, yes, that is a real keyboard in her toy stash. She loves "sending email" to people.
So, what do I want to do here?
Well...
I think the secret to me making this work is for me not to get over the top ambitious. For instance, I would love to paint this room (even just this wall), but I don't think that it's realistic to try to do that in the dead of winter. Instead, what I want to focus on is organizing her area better and making the space into a place where we can hang out better. You'll notice there's really only one chair (the old rocking chair) that doesn't belong to our main dining room table.
My goals:
Our main floor is composed of only two main rooms, the living room area takes roughly the front half of the house, while the kitchen, dining, family area comprises the other half. The ceilings are tall in both rooms. I think they are 10' in the front part of the house and 12 in the back part, since there is a step down from the front to the back level.
The play area is essentially part of the back area of the first floor.

This is the view of the western half of the room where Z's play area is located. There's a fireplace at one end and the sliding glass door out onto our deck. The floors are all hardwoods and all the walls are still (sadly) white.
This is the same half of the room, only facing north (the rocking chair is for reference). The door is to a small pantry. The window faces onto the deck of the apartment building next door and we don't get much light through it.
This is a better view of the toy storage. We are using an Ikea storage system because it is relatively inexpensive, flexible and the bins are cheap to replace. And, yes, that is a real keyboard in her toy stash. She loves "sending email" to people.So, what do I want to do here?
Well...
I think the secret to me making this work is for me not to get over the top ambitious. For instance, I would love to paint this room (even just this wall), but I don't think that it's realistic to try to do that in the dead of winter. Instead, what I want to focus on is organizing her area better and making the space into a place where we can hang out better. You'll notice there's really only one chair (the old rocking chair) that doesn't belong to our main dining room table.
My goals:
- Get a second toy storage frame so that the two can be placed back to back and Z can have an area to play on top of (this may be a little challenging since it's out of stock at both local Ikea's with no restock date... but I will persevere).
- Replace the toy bins and label them so that toys like Legos and Tinker Toys have a dedicated storage area -- hopefully this will also help others get the toys back to the right place.
- Get rid of the metal crates and get a real book case of some kind for her books.
- Cull out old toys she doesn't play with and find a place to donate/share/recycle.
Seems reasonable, I think. If I get really ambitious, I might consider art for the walls... but I think that needs to happen after the painting!

I'm with you on painting in the winter. I want all of the windows open for ventilation when I do anything like painting or sanding, which is definitely not something I want in the winter. If you could paint this room or part of this room a different color, what would you use?
I'm going to be having a spring of painting (recent insulating work has left holes that need painting over in nearly every room of the house), so it is something I'm definitely thinking of.
Here's an idea: Take pictures of the legos and stuff and use those as the labels for the bins. That way, as Z gets older, she can participate in helping to clean up her toys.
I always liked this style of book storage. I did something similar for my daughter. http://www.furniture-4kids.com/belo5se.html
And the picture idea above is great, starting them early at organization never hurts ;)
Bulletin or magnet board for Z art? Swatch paint while it's still too cold?
I need to do this project in our house! How about some fun and fresh wall decals to make it more her "area" before you paint? There are lots of styles these days. Also, chalkboard paint...you can paint almost anything with it (back of bookshelves, for example) and that's really fun! Hang child-friendly art at her level, perhaps. Or if not wall art, a mobile and a cozy play rug. I find the prettier the play space, the more fun it is to tidy for both child and parent.
Idea if you like it...If Miss Z has a favorite like butterflies, get a few wall paper versions and use them to decorate in the meantime. They come in a sticky version too, I think.
One idea for a matching bookcase might be Craig's list. We did this to get a matching shelf a few years ago.