[JavaBrewer]

The main question is how attached are you to your current neighborhood? Would you prefer to invest the $300K and have a home you want in your familiar neighborhood or would you prefer to relocate and move into an already done home? I have seen complete remodels (to the studs) take ~ 1 year, most take 6-8 months. Your neighborhood sounds incredible - the challenge IMO would be to strategically keep the charm of a 1950's crooked ruler home while incorporating the newer conveniences you desire. I would suggest you seriously consider exactly how much more space/rooms/baths you need and cut it down a bit from there. Focus on some high end finishing to give the home a timeless feel that you will enjoy for years to come.

Two years ago we moved from a modern 4000 sq/ft 2 level home into a 70's era 2300 sq/ft 1 level home. I sunk $80K in upgrades (me doing most of the labor) and honestly I am happier here by far.