Memory stopped being a big limiter on the desktop way before 2014. You'd want to go back to the 90s for it to be a major change in how things were done. So, back when people had 8mb of RAM or maybe 16mb if the machine was high spec and in theory Windows could run in 4mb. Swap existed but disks were so slow that if you actually hit swap then your machine would drag to a halt.
Anyway. No, it really wasn't cool.
The thing to realize is that software wasn't really that much better optimized for RAM than today. Maybe a bit, but mostly it just created a lot of pain:
- Every single API was specified to be able to fail due to OOM, and a lot of programmers tried to check for this and recover. However, there were no good ways to simulate or test it, and unit testing was in its infancy as a practice (e.g. no widely adopted frameworks for testing), and so in practice this just yielded a ton of codepaths and boilerplate that never really got tested and probably didn't work.
- Because RAM was so tight, you pretty much had to use the operating system's APIs for everything, even if they sucked or were full of bugs. It wasn't just RAM of course, it was also disk space, CD space, nearly non-existent network bandwidth. Duplication of what Windows had wasn't feasible. It meant everything was pretty consistent, which had its upsides, but it also meant that everything was consistently quite ugly and the horrible Windows/macOS APIs were all you got.
- Memory limits resulted in awkward APIs. No type safety, no enums (only bit flags), no reflection, lots of annoying (and by the late 90s obsolete) memory locking protocols that were holdovers from win16, and "rerendering" literally meant re-drawing small areas of the screen because pixels weren't cached. In particular a lot of APIs required you to call them twice, once to figure out how much memory something would require, and then a second time to fill out that memory once it was allocated.
- Error messages? Logging? Hah no. You get 32 bit error codes because there isn't enough memory or disk space for all the strings proper logging and errors would require. So you got really good at decoding HRESULTs.
- Garbage collection existed as a tech but because swap was so slow and RAM so tight it was very easy for it to trigger swap storms, so in common practice automatic memory management (when it existed) was all based on refcounting. So you couldn't quite just forget about it because you could still leak memory pretty easily even using a higher level language like VB.
The transition towards relative memory abundance was fairly painful. For example, Java because popular with devs because it had all those nice things that used a lot of memory but it led to slow/swappy apps that were painful for users. You still see the same complaints w.r.t. Electron apps, though today machines can take it and so it's more about people feeling it's wasteful rather than it literally killing the responsiveness of the machine like it used to be.
Of course in the above I say "was" and "used to be" but if you ever have to do any Win32 or low level POSIX programming you'll be right back in that world.