Current state of middleware. Thoughts?

Yes, it can be very frustrating for all the reasons you mention. However, once you find the right combo of packages it can be brilliant. Getting there could be easier.

Currently, there seems to be more disarray than there used to be.

Perhaps it depends on what tasks you're trying to accomplish via middleware. In my case, it is primarily related to producing CSS using SASS, implementing new CSS features with fall-back polyfills, and minification.

Some old standbys for these tasks have recently blown up. Packages I previously used successfully are now broken due to their dependencies having been updated... or not. In one case I resorted to using the node_modules folder from a previous project so I could get some work done.