I think the drawbacks of bundling are still not worthwhile even for TypeScript, but I'm not surprised that people who liked CoffeeScript would like TypeScript even more. It is unquestionably more useful; at least you get some value in exchange for having to spend most of your development time waiting for the build to finish.
What is mind boggling to me is just how popular CoffeeScript became. It makes no sense at all. I guess it just got a lot of celebrity endorsements.
I think the problem is that 'real programmers' held such prejudiced and condescending views of JavaScript that they were not willing to learn it and figure out best practices. They were too proud for JavaScript but they still needed to use it for their job so that's why they were prepared to use any possible alternative; better or worse - At least their ego was protected.
Same thing with TypeScript; its main purpose is protecting developers' egos by allowing them to leverage the power of JavaScript without actually having to admit to themselves that they're using JavaScript.
IMO, it's self-deception. JavaScript has proven itself to be an amazingly flexible, adaptable and backward-compatible language. It has flaws just like any other language but it's an objectively amazing language. It has proven itself.
Some developers will insist that it was because of JS's monopoly on browsers that it was successful but you'd be surprised by how many set top boxes and car navigation systems are powered by JavaScript (and they could have used any other language).
JavaScript achieved this in spite of being constantly undermined - The fact that it was able to grow and dominate in such adverse social environment speaks to how truly great it is as a language.