something not on walkthrough?

First time I played I received a task to obtain $20,100 in a time limit (i think it was 2 minutes).

First, how would you do that when it does not allow you to go over $20,000?

Second, the second time I played it did not pop up.....not sure why??

thanks

I never have more than 2 free workers to build, improve or clear things. Some tasks have 3 or 4 at least. I have lots of taverns and less people than my maximum. How do I get more workers free at the same time?