What I constantly ran into was disconnecting from the server I was connected to and wrangler not being able to handle that. At the time I had a somewhat spotty connection (nothing terrible), but it made wrangler dev very painful - so much so that I ended up writing my own node.js wrapper around it for local development. The lock-in to webpack also isn't great when I am nowadays accustomed to esbuild which is so much faster.
Happy to see miniflare now :)