Early versions of Delphi were cheap enough ($99) even a high schooler could pool the money to buy it (or, more realistically, ask their parents :-P). That lasted until Delphi 5 IIRC.
The real dumb move (though TBH i can only say that in hindsight) was that they made a free Linux version with Kylix, the license required any programs released to be under GPL but they didn't release Kylix itself as GPL.
This was in very early 2000s, when GPL wasn't the boogieman among developers that seems to be nowadays with all the permissive licenses, desktop software was still something people wanted, commercial software wouldn't touch GPL and yet a lot of new programmers were onboarding Linux. Having Delphi/Kylix full GPL with a CLA (like some other projects) would mean that a) Kylix would become part of various Linux distributions, especially during a time when distributions were the main source for tools for Linux users, b) anyone working on FLOSS would both use and improve the tool, c) mindshare among programmers would improve as anyone will be able to try it out for free (as long as they used Linux, but many programmers - especially younger programmers at the time - didn't mind that), d) companies, enterprises, etc that wanted to sell shareware or just didn't want the rules GPL imposed would still need to buy the full program
Sadly this seemed to be yet another case of when Borland started losing touch with programmers in the 90s.
For students and hobbyist, yes and was probably a dumb MBA lead decision because it stops the developer pipeline.
OTOH, As many tool vendors will tell you its foolish to dismiss a tool simply based on price. If your paying your developers $100 an hour even tiny improvements in productivity can easily pay for a $1000 or more tool. Just the compilation speed alone vs C/etc is probably worth the 5+ mins a day in savings.
It is, but it stops a large number of people from being conversant with your tool and that in turn almost guarantees market failure. I've got a super luxurious toolchain on my computer because of the free software movement and it may not be as flashy as what you can get commercially but it suffices for all of my needs.
The real dumb move (though TBH i can only say that in hindsight) was that they made a free Linux version with Kylix, the license required any programs released to be under GPL but they didn't release Kylix itself as GPL.
This was in very early 2000s, when GPL wasn't the boogieman among developers that seems to be nowadays with all the permissive licenses, desktop software was still something people wanted, commercial software wouldn't touch GPL and yet a lot of new programmers were onboarding Linux. Having Delphi/Kylix full GPL with a CLA (like some other projects) would mean that a) Kylix would become part of various Linux distributions, especially during a time when distributions were the main source for tools for Linux users, b) anyone working on FLOSS would both use and improve the tool, c) mindshare among programmers would improve as anyone will be able to try it out for free (as long as they used Linux, but many programmers - especially younger programmers at the time - didn't mind that), d) companies, enterprises, etc that wanted to sell shareware or just didn't want the rules GPL imposed would still need to buy the full program
Sadly this seemed to be yet another case of when Borland started losing touch with programmers in the 90s.