You can expect to earn $5-7k/month with no expenses and 5 months' work is about max. Where you spend the winter will determine if you can make it on that till next season. If you go to Venezuela, you'll live like a king. When I was there 3 years ago, I had to make an effort to spend more than $1k/month. Now I'm in Trinidad where you can live very comfortable on $2k/month.
About unemployment insurance I don't know anything.
Hope that this helps a little.