What I've got to clear out and why

I took this photo of my house today. I love to be cozy inside when it's like this outdoors and I enjoy sitting on the back patio when the weather is warm. I have lived here so long, and have so many memories that I am really attached to it. I know that it will be bittersweet to leave it when the time comes. The original structure is almost 100 years old and has had many additions. This is why the house doesn't seem to follow a typical style.

These are similar to the kind of house I would like to move into within the next few years. A 3-4 bedroom craftsman style cottage. Not too much to clean, lots of built-ins like bookcases, cabinets and drawers. I spent most of my growing up years in a 5 bedroom classic craftsman home. Although I didn't really appreciate it at the time, I had a big bay window in my bedroom. I regularly moved the furniture into different arrangements and many times, my bed sat inside the alcove of that bay.