Hello Brennan!
I'll answer you based on my own experience. I stretch everyday but what changes on my daily training is the stretch intensity. I mean, I push really hard one or two days on the week and do it lighter in the other days. You can do the same stretches everyday just changing the intensity or do different stretches but still considering the intensity. That's what work for me, but I think stretches and flexibility are really personal and you need to find what works better for you. Just be patient, practice and remember that the muscles need to rest to improve. 

Hope I've helped. 

I've been working on the 5 week Shaolin Total Wellness with everyone and we've been introduced to some newer (at least for me) stretches; really deep stretches. Just want to be clear that I haven't gone too far and pulled a muscle or anything like that, but I have definitely noticed that the next day or two after doing some of these really deep stretches, my muscles are really sore!!! Feels like I lifted weights and worked them out really hard, it's that kind of sore. Do you treat them the same way as if you had been weight lifting? Meaning do you try to up the amount of protein in your diet (and other things) to give your body what it needs to rebuild the broken down parts of those muscles? Is it important for the next couple days to do those same things again to get your body used to moving like that or is it more important to lay off for a few days and let your body recover?