Borland got greedy. Up to Delphi 5, the IDE was something anyone could afford at $99.95 with the cheapest option and going up from that up to $1000+ for the "architect" version. In Delphi 6 they made the cheapest option only for non-commercial use, still at $99.95 and the next tier was a few hundred. In Delphi 7 they made the non-commercial version free, but then they got distracted by .NET and started rising their prices hard to the point where the $1000+ version was the cheapest one until a few years ago. Then a few years ago they made a "cheap" $350 version but the license allowed only for $5000 annual income or something silly like that (they changed the limit a couple of times IIRC) and then you had to buy the next most expensive option which was several hundred dollars more. Lately they made that version free but the limit is still there. To add on that, most of the community doesn't really believe in the free versions since ever since the Delphi 7 Personal Edition they keep discontinuing them (they made another in 2006, based on the slowest and most buggy version which wasn't exactly a great idea) and then bring them back years later with different limitations (and always the reason for discontinuing them is that it didn't work - as if they'd magically become popular in a few months for releasing a free yet extremely limited version).
Add to that that after Delphi 7, which by many was considered the most stable and generally best version, they got distracted by .NET and Linux (with a very hacky project, Kylix, that never got any traction in the Linux community) and decided to make Delphi a .NET product, rewrote the IDE with a highly unpopular (at the time) interface with a lot of bugs and generally a much worse experience for developers and you get the idea.
They basically did the worst thing they could ever do at every single front: abandoned their core audience (Delphi was very popular with smaller developers, especially in Europe) to go after enterprise customers, closed the gates to new blood by increasingly rising the prices, created a sense of unreliability by changing their minds every few years, replaced a stable product with a buggy mess and drove a lot of their skilled people to leave over the years.
The same stuff apply to C++ Builder too, btw. They actually lost a chance here - C++ Builder could have been a the IDE to use for tools in the game industry that relies a lot on custom tooling and some developers did try to use it (e.g. Bioware and i personally worked on another company that also considered it) but Borland/Inprise wasn't very cooperative and they left their C++ compiler stagnate (in our case the compiler simply couldn't build the codebase due to outdated standards support).
Delphi and C++ Builder are products that you can't help but wonder what they could have been at the hands of a company with more competent management.
Add to that that after Delphi 7, which by many was considered the most stable and generally best version, they got distracted by .NET and Linux (with a very hacky project, Kylix, that never got any traction in the Linux community) and decided to make Delphi a .NET product, rewrote the IDE with a highly unpopular (at the time) interface with a lot of bugs and generally a much worse experience for developers and you get the idea.
They basically did the worst thing they could ever do at every single front: abandoned their core audience (Delphi was very popular with smaller developers, especially in Europe) to go after enterprise customers, closed the gates to new blood by increasingly rising the prices, created a sense of unreliability by changing their minds every few years, replaced a stable product with a buggy mess and drove a lot of their skilled people to leave over the years.
The same stuff apply to C++ Builder too, btw. They actually lost a chance here - C++ Builder could have been a the IDE to use for tools in the game industry that relies a lot on custom tooling and some developers did try to use it (e.g. Bioware and i personally worked on another company that also considered it) but Borland/Inprise wasn't very cooperative and they left their C++ compiler stagnate (in our case the compiler simply couldn't build the codebase due to outdated standards support).
Delphi and C++ Builder are products that you can't help but wonder what they could have been at the hands of a company with more competent management.