The packages were structured that some really nice features were bundled with stuff many likely would never use and the upcharge to each tier wasn't small.

If you are buying for yourself, then it is 199 euro which is less than half the price (although that doesn't include VAT).

A commercial new license is $500.

Not sure where you get the big price drop from ;) And yes, it is easily worth $500.

It goes on and on. When I considered it for a project the cost came out to almost $5000! Instead we went full open source (including JetBrains' open source version of PyCharm) and got lots of functionality one couldn't find at any price on the Delphi platform - which incidentally is, just now in 2015, beginning to set up package management. Unfortunately it will be tightly controlled by Embarcadero and they've issued all sorts of warnings about not approving code that replaces functionality in Delphi (in short, they're afraid of competition). The community has no control over the language or the product and the diehards that are left treat it like a religion. They have something called "MVPs" who actually sign a contract to never disparage the language or Embarcdero! In exchange for selling their integrity they get free copies of the product. Completely coincidentally, they'll tell you that the product isn't overpriced. They'll also tell you it's used all over but no one talks about it because "it's their secret weapon". Delphi's product manager told me that he fully believes that "Delphi has had a greater impact on the business world than Python ever has". You not only have to pay all that money, you have to deal with the Scientology of programming languages. :-(

So no, you pay far more than for IntelliJ, you have no control over the product, you have no working roadmap, you don't even have RELEASE DATES for new versions. It's a whole other world over there than what the rest of us are used to.