Montevideo is a city in part defined by what it's not: it's not Buenos Aires. Tourists to Montevideo often are coming from BA or en route to BA and treat Montevideo as a stop-over. This understandably generates a certain amount of defensiveness on the part of Uruguayans. Tourists looking for flashy big city action are too quick to dismiss tiny Montevideo and all its humble charm, but locals, too, are too eager to point out differences or Uruguayn superiorites which flatly do not exist.
All in all, I had a lovely stay in Montevideo, and I would certainly consider living there. It is probably a city better to live in than visit, though even a short-term visitor like myself had plenty to do and see.
The relative smallness of Montevideo lends itself to walking, and walk it I did. I was staying in Ciudad Vieja (old town) but walking to the different barrios, or to the waterfront, didn't take long at all.
After arriving by ferry from BA, I met up with a reader who was super gracious with her time showing me and other friends of hers around town. We had coffee in an ultra-hipster cafe which implored on a sign inside, "Don't tell other people about this cafe." Which of course is wondefully counterintuitive viral building marketing.
At night we ate at a typical meat restuarant (meat is eaten perhaps even more in Uruguay than in Argentina) and then went to a house party / birthday party at an apartment. Fun seeing local and ex-pats mingle. As always the language of choice was Spanglish, or mostly Spanish. Always interesting to see how locals react to very American looking Americans. Some harbor knee-jerk resentment; others knee-jerk curiosity; others simply display a univeral friendliness to all comers. (Uruguayans are friendly folk.)
The following day I checked out the town by foot and then at night we went to dinner, then hung out at a park which was epic in its own way, then a bar with a dancefloor downstairs. Montevideo seems to have plenty of nightlife options — BA seems to have almost too many options. But both Montevideo and BA start LATE and end LATE. Sleep deprivation: it's a way of life.
Along the way I had two chavitos, which is the national sandwich (how cool is that?) and kept buying more agua sin gas than probably anyone else. Thanks, diabetes.
Bottom Line on Montevideo: Come, visit, spend a few days, then head to the east coast. I'll be back, Uruguay!