Ummm... I hate to break this too you, but you must define a "Utility" function in order to answer these quesitons. If you are talking about "Expectation", that is the same as a utility function U(t) = t. This means that $1 when you have none is just as important to you as $1 when you already have $1,000,000.
In the first one, your expectation is -$10.00 + (1/30)*($300), or, a maybe little less confusing (29/30)*(-$10.00) + (1/30)(+$290.00). Again, though, we can't really talk about "Utility" until we know the Utility Function.
And just for the record, there are subjects worse than Statistics. Statistics is FUN!