I'm also of the opinion that compiling assets in production as a part of your deployment process is insane, there's so much magic in the Rails asset pipeline that it's not uncommon to turn up bugs where tables don't exist, and the rails app can't initialize, or some javascript runtime environment isn't found which can leave your deployment in a broken state.
I'm firmly of the opinion that assets should be compiled and checked in, but then of course you run into problems with rails serving those in development mode, rather than the development files.
All these issues are fixable, but they're all indicative of tools that aren't quite mature yet, and as Capistrano sits on the boundary of where these problems come to light, it seems to fall to us to deal with it, and to educate people on what they ought to be doing.
Education is no problem, I really believe that the de-facto standardisation of Rails-like deploys (i.e timestamped releases, with common linked directories, and a symlink to the current active timestamp) is an excellent result for knowing what to expect in an environment where there's hundreds of ways to get Rails apps running, but it's still not as smooth a process as it could be.
I'm familiar with at least one project that's been re-written in Scala and Java because the previous version was prohibitively difficult to deploy as it was in RoR. (GrayLog2, to namedrop them)