I totally agree with #1. Deployment is a real weak point. It can be done, even using Capistrano if you're willing to put up with it, but it's nothing like what it could be.

With respect to #2, I strongly suggest you reevaluate. Strongly-typed views will save you a lot of boilerplate code in your controllers and HTML helpers only interfere with your markup to the extent you want them to. Most of them are super minimal and easily styled or manipulated. I expected that the helpers would just be different ways of getting into the same mess you encounter using things like server controls in webforms but I was quickly shown otherwise.