at.algebraic topology - visualizing what's going on in based homotopy theory, et al.

I'm reading J.P. May's Concise Course in Algebraic Topology, and I'm having a lot of trouble visualizing how things work in Chapter 8, "Based cofiber and fiber sequences". Of course this is pretty basic stuff, but it's really cool to me that there are such clear topological analogues to the usual exact sequences in homological algebra. Still, I can't even get a clear picture of what a smash product looks like for any but the most basic of spaces, and based cones/suspensions/loopspaces make my head hurt.

a) Will I be alright if in my head I just sort think of a smash product as a usual product (for example), with the understanding that I need to tack on an extra condition that I really shouldn't think too hard about?

b) Why all the fuss about based homotopy theory, anyways?

c) While I'm at it, can anyone suggest a book that is less terse? I feel like this one rarely gives the motivation and visual intuition that I'd like...