For the first 5 years of my woodworking hobby I was in the military, so had an added irritant to deal with in regards to my woodshop. About the time I get it set up the way I want it, I have to move. Same goes for wood supplies and anything else that you buy locally.
One upside though is that I kept getting bigger shops. Started out in Dayton OH with no garage, moved within Dayton and got a one car garage. I was then transferred to Oklahoma City OK and then I had a two car garage with a shed in the backyard for those pesky things like lawnmower and excess lumber storage
In 2004 I separated from the military and returned to Northern Minnesota and bought my first house. I found a house that had a 26x32 garage with it. Another upgrade for the workshop!
In the fall of 2009 I started on my dedicated woodshop. I have been planning this shop since I bought my house, and was finally able to get started. Check out the build progression here! I completed it the summer and fall of 2010.