I think I know the answer, and the question has been asked and answered in the past, but I thought I would get the advice of Los Expertos en Uruguay based on my particular circumstances.
I will arrive in Montevideo on late on Friday, November 8, and leaving Tuesday, November 12. In fact, I arrive so late on November 8, that it will actually be the morning of November 9 (1:30AM). This means I have four nights, but only three days in the Uruguayan capital before I hop in a rental car and drive to La Paloma for three nights. This is a pleasure trip. I have no business in town (although wi-fi in the hotel is essential to keep up with business at home once a day.) So where do I stay?
These seem to be the choices:
(1) Centro / Ciudad Vieja. I have a limited amount of time. This will put in the middle of the restaurants and nightlife, and a close walk to the main tourist sights during the day. I won't have to take a long cab ride to get anywhere. Besides, I am going to the beach later in the trip, anyway.
(2) Pocitos / Punta Carretas. I'll have to take a cab anyway, at night at least, to get anywhere since Centro is not safe to walk after dark. Hopefully, cabs are cheap. So, I might as well stay someplace safer, quieter and beautiful.
(3) 2 nights in Centro (Friday/Saturday), then move to Pocitos or Punta Carretas for the last 2 nights. It's my first time in Montevideo. I might as well get a feel for as much of the city as possible.
One other note, because I will not be getting to my Friday night hotel until 2:30 or 3:00 in the morning due to the long flight, does this mean I have to book a room in large chain-type hotel to make sure the front desk is operational at that time?