Alright, so many misconceptions to clear, where do I begin?! I don't even know if it's worth clearing them, or to let them fly and keep Eastern Uruguay a well hidden treasure...
Punta del Este and its countryside (Maldonado "county") is indeed what could be described as a little piesce of heaven particularly off season, during the months of March, April, October and November.
Yes, winters can be a bit chilly (while summers are hot and dry) which fits its description of a perfectly Mediterranean climate only found elsewhere in Southern Australia, The Cape, Central Chile and southern California (and the Med of course!)
First of all, while the population exceeds a million during the peak summer season, it doesn't shrink to 50 during the winter, rather to a good 100,000+ comprised by locals, expats, argentines who moved permanently, and 200,000 sea lions.
The megamall is therefore open all year round to service this rather affluent winter population and its supermarket "Tienda Inglesa" is well stocked with a cornucopia of local and imported products, all year round that puts any Argentine shop easily to shame.
Gas stations, also open 24/7 365 days a week, sell a decent variety of essentials, and unlike Argentina they also sell alcoholic beverages and do take four currencies - legally.
Everybody does, and conversion is free and unregulated for sums less than 3K per transaction. Uruguayan peso, Argie peso, Brazilian Real, USD, and Euro.
Punta del Este (and Piriapolis, Punta Ballena, Jose Ignacio, La Paloma, La Pedrera, etc) is indeed more expensive than Argentina but the quality of the products more than makes up for it.
Rentals from March to November are dirt cheap for luxury apartments, but they hike tenfold for the summer months.
Building is not cheap either (land IS), but it can be offset by renting during the peak season. Some buildings were designed exclusively for summer use and therefore lack proper heating, but HVAC alternatives are responding to the market.
The natural beauty of the rocky outcrops, beaches, marine fauna, woodlands, lagoons and rolling countryside is free of charge....
Both Chui and B.A. are a daytrip away so buying stuff in Brazil or Argentina is also a monthly option. By Chui I mean the border with Brazil, where they don't ask you for a freaking visa just to buy some stuff on the other side of the artificial line and go back to Uruguay.
Uruguay is very receptive of English speakers, not just Americans, as it has a long story of friendship with Britain. It is the least Catholic of Latin America.
Culturally it's more European than Portugal.
(Everywhere except in Montevideo) Social tension doesn't exist as even the poorest understand the concept of mutual benefit thanks to 100 years of tourism, and service-oriented thinking, and the fact that people help their neighbors to a reasonable extent.
People in general behave in a manner that albeit maybe too relaxed, would be described as "sane"
Finally, the thread opener obviously does know how to surf the web since Punta del Este was founded by portenos who couldn't stand buenos aires anymore, and therefore asking about Punta here makes as good sense as asking about Montauk while in Manhattan.