I personally have not had any luck trying to dose on mutiple substances over the course of several days. The one time I did I tried it at a festival a couple years ago. I took ketamine the first night, doc the second day in the morning, then redosed in the early evening (4 mg total) and then I took 100 mg of mdma that night. I woke up the third day still tripping. The evening of the third day I took 4 hits of really good lsd and a "thumbprint" of mdma and felt NOTHING. I felt completely sober.
I would recommend rolling on one day and taking shrooms on the other. Trying to roll two days might prove to be fruitless, you may feel *something* on the second day of rolling, but most likely it won't be optimal.
Just my $.02