1. Grew up on a farm in a 150+ year old house.
2-5 - various lodgings, shared houses when I was in college.
6. one year living in a house in town with my parents between 1 being sold and the 7 being built.
7. New bungalow built for my parents
8. Living with a friend of the family in the big city. Spent almost a year sleeping on a mattress in her bedroom, then another 8 months or so in my own room after her lodger moved out.
9. Living in a shared house with people I'd never met before I moved in. Lots of random people moved in and out in the five years I lived there.
10. Living in an apartment with a friend from college with whom i'd shared most of 2-5.
11. Another apartment in the same complex as 10, also with friend from college.

Of them all, I think my favourite would have to be 1.
I grew up there, and while it might have been a bugger to heat and was fairly isolated, the rooms were spacious and I loved the peace of the countryside.
Least favourite? Well some of 2-5 were pretty grotty, but I was young, I was in College, and it really didn't matter. I'd say I was least happiest in 9, but I'm well out of that now.