I plan on breaking the far wall out (right of the fireplace) and replacing it with windows and sliding glass doors. This will lead to the back yard and a patio + pool. The fireplace will be replaced with a gas one and rebuilt to match the style of the house and look like it's always been there. It's in pretty bad shape anyway. The floor will be terrazzo. This is roughly a 2016 thing.
With the roof, the gameplan is to do something with it to move away from a traditional ranch. At the same time I would like to enlarge the windows to the full size of the opening in the brick. At this point it's unclear whether this type of roof or a butterfly roof would work out better but tying into the existing roof structures will be an issue that needs to be addressed. It's really hard to get a decent idea of it from my PPT photoshop job...
Please excuse the world's worst fence. The structure to the left is part of the 2002 addition.
The garage was added in 1979 and not tied in well to the existing structure either. Water intrusion has been an issue in the past.