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Craig,
My first advice would be to tell your wife to hold on for a few more years.
In terms of jobs, a good paying job in the Maldonado area (involving taking a bus to Punta del Este daily, with a one hour or more commute each way) would pay you at best US$500 per month. In Piriapolis you would earn more in the US$300 region.

With children, and a decent lifestyle, you would be spending in the vicinity of US$2,000 if you kept things very frugal, or more like US$4,000 if you want to send them to a decent private school, for example. There is no way to make that kind of money unless you are an independent professional (lawyer, doctor, etc.) or run a very successful business here.

Opening your own business is something you never should attempt until you´ve been in a country for at least two years. Businesses in Uruguay in general are "scrape by" situations, so although a pharmacy could fulfill your goal of setting an example for your kids by going to work, down the line they could question your financial and business decision-making skills

Lastly, beware of the relatives. You would be a rare exception if not approached by one, a few or a horde of in-laws downright attempting to borrow money for life-or-death (if you don´t lend) situations, or offering you brilliant business opportunities. You are and forever will be the gringo with the deep pockets in your family, and the earlier you learn to say no, the less money you will lose.

So, again, explain to her that it´s not such a great idea to return until the kids are a bit older, you don´t need to worry about your savings and you´ve researched your plans on the ground for a few years at least.

Visit Uruguay with an eye to living and doing business here, talk to all the expats you can (there are expat groups meeting along the coast all the way from Colonia to Punta del Este), crunch "real" numbers collected during your research, and prepare the move thoroughly.

Hi,
Thanks for the advice. We just got back from uruguay 3 days ago. We decided to spend two months there in the winter to see how we would like it. I must say that the winter was not as bad as I anticipated. Piriapolis was very quite except for a few weeks when the children had their winter break. We did stay in Salto for a week. The weather there is much better. The children enjoyed the water park. After spending these two months in Uruguay I have come to a few conclusions:
1. As a family we seem to be closer. Probably because there are not as many distractions that we have here in the US and the cold weather keeps in the home together.
2. We did find plenty to do in the winter (punta shopping, walking on the beach, horse back riding, searching for pine cones for the fireplace, etc)
3. We did not have to spend a lot of money to have fun
4. Piriapolis is quite at night, Punta is not much more alive but at least it is alive.
5. Finding people to fix our home and make furniture was a pleasurable experience. (I think the people of Uruguay make the country a nice place to live)
6. There is just about no way we can start a business and expect to make a decent amount of money in Uruguay
7. We are looking into the possibility of purchasing properties that we can rent during the summer. It looks like a decent way to make some income.
8. (The MONEY) The relatives have been pretty good.
A. Wife's mother has her pension and her husbands pension to live on. Occasionally I will pay for her airline tickets, but nothing extravagant.
B. Wife's brothers live in Barcelona and make good money. They have never asked for a dime.
C. My wife seems to be more conservative than i with respect to giving money to her family.

I appreciate your advice and input.
After spending two months in Uruguay my wife seems to have changed her mind with respect to moving back so soon. I guess those cold, rainy, windy days are having her think twice.

We are interested in purchasing land that can be used to raise cattle or sheep. Do you know of anyone who i could contact to make some inquiries?

Thanks,

Craig