So I tried 2 of the 3 methods, the last one being the one where I apply the numbers on a strip then bend it to make a cylinder.
The boolean worked well but if I have to connect all the edges from the boolean operation to the edge of the cylinder I'm losing the roundness of it in some areas.


The bump looks god from far away but if I get too close the edges are not sharp at all, I have a smooth iteration of 4 and for some reason it doesn't let me go higher.
My bump map looks just like diffuse map with sharp edges, didn't add any blur to it.
That's how it looks:


What do you think, how could I get a clean result?