Yeah, what coolwhip said about the amp and mic. Actually, a small tube amp would be best for that, since generally effects (not modellers, just effects) are designed to work with tube amps. Go out and get yourself an Epiphone Valve Jr. and if you really care, replace the tubes and the speaker, it makes the tone much richer.
About order: probably the Boss before the preamp, but if you end up introducing more into your chain you can screw with it. Some of the most innovative sounds (see: Hendrix) come from putting things in strange orders, like fuzzing a wah, etc.
Just my two cents.