After seeing Mikiem2's discussion yesterday about the older audio software, I was reminded of some thoughts I've had recently concerning older software.
What's wrong with old? It usually still works fine!
Recently, I got into the mood to play the ORIGINAL Treasures of Montezuma. It was given away years ago here and has been in the freebie circuit for years. However, many sites, including the original developer, Alawar, have "retired" it. The copy I currently play came on an old CD of various old games. Regardless, it works absolutely fine on both Windows 7 and Windows 8.1 so I see no reason it would not run under 10 as well. The only problem -- it's OLD!
Last year, I got a laptop and transitioned my games onto that machine as well as all subsequent games I've gotten. I currently have 1457 games total across the two machines. 99.2% of the games have transitioned to the new machine with only 11 failures (one recent one) and 15 that I skipped (decided not to even try -- mostly old DOS games - because I didn't feel like fussing with DOSBOX). Most of the failures are not the OS but the graphics card on the laptop. Even some of the "successes" have a few hiccups due to graphics issues.
Last year (and again this year), I replaced my printer. The latest replacement was with the exact same model hoping to keep the weird print driver (didn't work). The printer and driver are "new". The driver is supposed to work with all versions of Windows from XP through 10 (according to the combined info from the 2 CDs with the same driver version number). However, the only software I have been able to get the driver to work with is Internet Explorer and Foxit Reader. Everything else is too "old". Even software that was just released a week before I got the latest printer ("old"?) fails.
The prime failure is Microsoft Office 2007. Yes, Office has upgraded several times since 2007. Yes, Excel has a weird problem with sorting that is supposed to be fixed in the 2010 version. However, it works fine - does what I want - and I don't want to pay again for features I don't know about and may not need!
Again -- what is wrong with old? I'm not saying there's anything wrong with new but if what you have works and you would have to pay for an upgrade to what you already have, why bother?
I guess the only answer to the question is the developers can't get MORE money from you if you don't upgrade. But if the software is so poor that you HAVE to upgrade to get it to work, then I suspect other ways would be found -- like competitors!