The decision
Vitamix is one of those products that sounds ridiculous until you use one. It's a blender. Why does a blender cost that much? Then you make something that would leave a normal blender rattling, stalling or smelling faintly electrical and you understand what the money bought.
That doesn't mean everybody needs one. This is where frequency matters. If blending is a real part of how you cook — soups, sauces, smoothies, dressings, frozen things, purées — Vitamix earns its place. If the blender comes out twice a month, spending hundreds of dollars on it is solving a problem you don't have.
The cheap one has a trick
The reason I like the Oster isn't because I'm pretending it's secretly a Vitamix. It isn't. I like it because it is a straightforward blender at a straightforward price, and the glass jar is a feature I genuinely prefer over a lot of cheap plastic blender jars.
It will blend the margarita. It will make the smoothie. It will handle a sauce. If that's your list, stop shopping.

Vitamix 5200
Powerful, simple and built around doing the actual job extremely well.
CHECK AMAZON
Oster Original
The glass jar matters. For basic blending, this is a refreshingly uncomplicated way to spend less.
CHECK AMAZONWhere I'd put the money
If I were building a kitchen from scratch on a budget, the Vitamix would come later. I'd buy the good chef's knife, thermometer, pans and cutting board first. But once the basics are covered, this is exactly the kind of appliance where I'd rather buy the good one than work my way through two mediocre ones.
The one I'd buy
Vitamix if I know I'll use it. Oster if I have to invent reasons to justify a $400 blender.