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Your images are unreadable, can you upload better quality images so we can read your model?
Are you familiar with the concept of a sub-model? It is literally nothing more than you dragging a pre-built model into another model when in model builder.
You can only have 1 iterator in a model so you you cannot create a loop within a loop by sticking 2 iterators in 1 model. The solution to this is to put the second iterator and the connected logic in its own "sub" model and then drag the sub model into the master model and connect it up.
To pass outputs of a tool into the sub model you must set the inputs of sub model as parameters (right click on them and set as parameter so you get that "P").
Hopefully you understand above? Well if it were me I would create a master model with your logic up to your "field to build raster calc". As I understand that is a polyline featureclass with a month field?
Now create new new model which has a feature selection iterator as it start with the case field being your month and chain the logic of polyline to raster to cell statistics. You would then use inline substitution to give your final output a unique name, in your case based upon month ID.
You then drag this model into the master model and connect it up.