a) Immediate Mode has been out of fashion for since before the turn of the century. Even the good old NVidia GeForce2 of 1998 already had OpenGL extensions that are essentially vertex buffer objects; you can in fact use the GL_ARB_vertex_buffer_object extension on a GeForce2. If you don't believe me, I'm currently headed to my mother's and I have a old box stored in her cellar with a GeForce2 in it; I could give interested parties a SSH into it (you just have to live with a old Gentoo installation that I didn't touch for some 10 years or so).

b) There's a certain complexity cutoff where the whole shader loading boilerplate plus shader code is less, than what it takes to setup an equivalent fixed function pipeline setup. Making an educated estimation I'd say, that the break even point is, when enabling a register combiner on two textures, one a cube map, the other a normal+shininess map, setting DOT3 combining of normal with vertex secondary color (for normal mapping), directing the normal map into the cubemap texture coordinate lookup and fading between reflection and dull shader based on shininess. Sounds complex? Indeed it is, but keep in mind that this kind of thing was already possible with the GeForce3 (at least, I think it may even work on the GeForce2, but after over 14 years since writing the last time a program targeting it, I'm a bit shaky on the details).

Anyway, to set up this kind of register combining you'd need between 4 to 5 calls of glTexEnvi per texture. Another 3 glTexEnvi calls for setting up the secondary color muxing mode and another 3 calls for setting the final stage fading mode. Add to that the hours of twisting your brain to figure trying to wrap your mind around all the relevant state switches in the register combiners.

With shaders you simply write down what you want.