I lusted after a Vitamix for years, but when I actually got to try one (visiting friends who were into raw food) I was underwhelmed.
I've actually never owned a blender, instead I have a Cuisinart food processor, which works great for making smoothies (and nut butters) and it much easier to clean than any blender I have encountered (the blade comes out, so no digging around under the blade to get things out). I have had mine for 12 years now and it is still going strong. My parents had basically the same one when I was growing up, they got it as a wedding present and didn't replace it until I was in college (so at least 20 years later). I use it multiple times per week (I have a smoothie 2-3 days/week, use it for slicing and grating big batches of vegetables as part of our weekend meal prep, and I also use it for something like making nut butter, seitan dough, hummus, or oat flour almost every week). In terms of saving time, money, and facilitating healthy eating, I think a food processor is a MUCH better investment than a blender, as it can do everything a blender can do...and then a whole bunch of other stuff too.
It does not deal well with ice cubes/frozen fruit (it will grind them but the racket is terrible and I suspect it would eventually kill the motor), BUT...I dislike my smoothies ice cold. So my solution to this problem is usually to add a little boiling water to anything that has been frozen, which generally breaks the frozen stuff down enough not to be a problem. Alternatively, if you are making smoothie kits, you could move your smoothie kit from freezer to fridge the night before, so everything would soften up a bit overnight.
It does not get things quite as smooth as a vitamix, but it gets stuff pretty darn smooth. It's not good to break down your kale smoothie too much anyway...you lose some of the fiber benefits :)
If you make a lot of blended soups, I find a really nice extra blending tool to have is an immersion blender, so you can just blend everything in the pot it cooks in. This allows you to easily make a much larger batch of soup than you can with the Vitamix (or any blender, really). The immersion blender is also much easier to clean up.
So in conclusion, no, I don't think a Vitamix is worth it. Cuisinart food processor and immersion blender for me :)