Hi Jack!
What follows is something of a non-answer because I do not think there are particularly good answers to your questions - there are so many variables that depend on what You are creating.
And, like @TKDblackbelt I have not used Webflow - but I did read reviews of it as well as Wix, Squarespace & Weebly. Even those relatively similar "drag'n drop" web site builders have different niches.
Hype is an animation program - a tool in your toolbox. I do not see it replacing a full on HTML web program. However, if it is a relatively small site with lots of animation then Hype might be a good choice to create the web site. Or if it is a simple site, or one that needs to be created on a low budget, Hype allows for quick assembly. (This is what iWeb was so good at).
Of course You can build complex sites with Hype - I just don't think it is the right tool for the job.
The flip side - Hype is an invaluable app in the role it was designed for - and the Hype community is the best I've ever experienced. Why not check Hype out and see where it fits best in your workflow? It is great software.
So all things considered... your final thought might allow the most flexibility in your work.