Answer
$12$ crossings, $96$ dollars
Work Step by Step
Step 1. Assume $x$ crossings are needed.
Step 2. Without the pass, the cost is $8x$
Step 3. With the pass, the cost is $36+5x$
Step 4. Letting $8x=36+5x$, we have $3x=36$ and $x=12$ and a total cost of $8(12)=96$ dollars per month for both.