I'm a little biased on this because I worked for Wendys for a long time. I will tell you now:
-Chili is best when it's a day or two old because more of the water has evaporated and it's all nice and thick.
-Pay for a coffee and a small vanilla frosty, but have them simply put a small amount of coffee into the bottom of the frosty. Mix it up and enjoy a REALLY GOOD coffee milkshake. If they like you perhaps they might be willing to add whipped cream and chocolate sauce. MAYBE.
-In October every year they offer jr frosty coupon books for a dollar. Go ahead and take it, you don't have to order anything else with it. It's 10 free junior frosties.
-Fish sandwich is only offered during Lent. We get asked about it year-round.
-I'd be happy to answer any questions.
For the record, Taco Bell is the worst for me because I get sick every time I go to one.