Step 1 :Define the total number of envelopes as 6.
Step 2 :Define the number of envelopes containing a $539 check as 3.
Step 3 :Define the number of envelopes containing a $1000 check as 3.
Step 4 :Calculate the probability of selecting an envelope with a $539 check as \( \frac{3}{6} = 0.5 \).
Step 5 :Calculate the probability of selecting an envelope with a $1000 check as \( \frac{3}{6} = 0.5 \).
Step 6 :Calculate the expectation as \( 0.5 \times 539 + 0.5 \times 1000 = 769.5 \).
Step 7 :The person's expectation is $769.5. So, the final answer is \( \boxed{769.5} \).