[mwcampbell]

Where do you think your understanding went wrong initially? You said you realized that doing anything in the old system was slow. Was it not actually slow? Was the slowness not relevant because there weren't actually that many routes? Were your coworkers resigned to having some minimum level of tedium in web development? Or something else?

[eropple]

Oh no, it was slow--but it was slow and they were used to it. (And there were plenty of routes--probably somewhere close to a thousand at the time, in 2011?)

The problem I hadn't fully understood was a mix of the last point you suggested--tedium's just how it is--and a set of libraries built up as coping mechanisms that were intrinsically tied to the servlets process. Not really written to be able to be shimmed into a better world without dragging the whole thing there, and not enough appetite to try for it.