I was rather surprised about 12 years ago when we were looking to move in together, and someone told us, "oh, you can get around this building's no dogs policy with a doctor's note." That really bothered us.
We ended up moving to a place that was within walking distance of a great dog-friendly (on the patio) bar. I walked our dog there nearly every weekend!
There's now a restaurant in town (Massachusetts) that proudly claims their patio is dog friendly. I might take advantage of it when my puppy is a little calmer.