For the most part I like my current house, despite most people's tendency to think of it in horrible condition. Partly my attitude changed because of my over all attitude changing, but also partly because we've taken a break from trying to fix some of the problems and just live with it. In general the house is sound, paid off and in a decent location, especially for G.
Every new prospect makes me think about the money, about the hassle of moving, the nail bitting ride that selling this house will be, and about the inconvenience and trouble it will be for G to no longer be walking distance from the red line.
So it makes go back to why. There are definitely things I still very much look forward too (a garage, a shop, a higher percentage of the house to modern code, not fearing that my neighbor might be seeing me naked, not needed a white noise generator because of excess street noise, closet space, central air, etc.) but since the hassle is unknown and some part of the gain is unknown it's hard to weigh.
Add in that the money issue, which is even harder (what do we have money for but to improve our lives, but will it be a mistake to take money our investments for more house than we really "need."
So not really any answers, but I wanted to sort out my thoughts and write them down to see if I had an revelations.