I have had a few pups with varying degrees of collapsed trachea.
When you say you chose medical management over surgery, I am assuming you mean for the trachea? There are many ways to manage it medically. First and foremost, keep her weight within normal range, keep her calm and cool. Heat and humidity can irritate them. I have had times where I would take a pup into my car and put his/her face up to the a/c vent. It helps sometimes!
What are you doing to do about her teeth?
I don't know how bad your pup is, but I can tell you that I have had pups live long lives with CT. I have had some that didn't do as well, but it is not an automatic death sentence.
Welcome to YT! Look forward to getting to know you and Piper!