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As an expat in Uruguay, and probably not a spanish speaking family, you have two school choices, the American School and the British School   You should check out their info on your own.

As to living expenses, well, as an American who travels there a few times a year I can tell you that renting a car is VERY expensive, fresh food is generally cheap, and restaurant costs are the same as an avge American restaurant of similar quality, though how that translates to where you live I have no idea. 

Everything that is imported costs about 140% or more then what I would pay in the US.  A $600 laptop will run you $1000, etc.

There are lots of nice places to live in Montevideo, and plenty of places not to live.  Much depends on where you work, and where your kids go to school.  Carrasco is very nice, but on the outskirts of town.  Living in the city in Pocitos or Parque Rodo or a few other areas are nice.  You really should gte a real estate person ot show you around and discuss things with you.  If you do not know of one who speaks english I can set you up with mine, who does.

In general Uruguay is a great place, and I love it every time I go there.  You WILL need to learn some spanish as English is not highly used, though the USDollar is!  And spanish there is much like Castillian Spanish of Spain with the soft 's' sound, not the hard 's' of Mexico or as spoken in the US.

Bus service is excellent and cheap, and will take you anywhere.  If you stay in a nice area and travel the main routes, you should never have anything to worry about.  People stay up and out late there at night.