I wasn't a fan of the 6.x series of DOS but I can't remember exactly why. I have fond memories of DOS 5.0, but that's also the first version I ran on my 486 that we built in the 90s (I came from an 8088, so this was an unfathomable upgrade). It was the first version of DOS that I could finally run some interesting games on.

One thing I do recall about the 6.x series that drove me nuts was that the installer progress bar was ... peculiar[0]. It seemed like you could benchmark the 5.0 and 6.22 install from the time the progress bar started and both would go from 0% to 99% in the same time, but where 5.0 would finish with a non-unusual delay after 99%, each version of 6.x spent a while there, with each minor version longer than the prior. By a while, it was something like 3 or 4 times more time spent on that 1% than the entirety of 0-99 (no politics intended). We joked that the entire MS-DOS 5.0 installer must have been copied over and they appended all of the files for 6.x to some post-install script that ran at 99%. No evidence or attempts to gather evidence were ever done, but it was something to talk about while waiting for that last semi-solid 8-bit ASCII block to get filled in.

The 6.x series ended up being one that I ran for the least amount of time -- I ended up on DR-DOS and PC-DOS. But software of that time was really painful to work with. Eventually, I ended up on OS/2 (2.0 through Warp, which I used until just prior to Windows 95) because it felt like the software I depended on ran the same on the platform it was designed for -- Windows 3.x -- as it did on on OS/2's compatibility layer[1].

And the worst part is this is not a compliment of OS/2. Back then, starting an application wasn't as simple as tapping an icon on a touch-screen. Some programs required commitment and following a careful launch sequence if your level of commitment was detected as insufficient. To appease these demonic applications, you followed a careful set of ritualistic actions. Double-click the program icon, wait until the mouse stops moving entirely (or if it starts hopelessly stuttering, that's fine, too). At this point, turn the computer off, wait until it's quiet, turn it back on, tidy your desk, refill the coffee, double-click the application icon (rinse, repeat until you land three 7s). And in the days of co-operative Multitasking or OS/2's 'hold my beer' with a single application's bug taking out the entire system (OS/2 one-upped Microsoft by occasionally causing dumpster fires in the shape of large, metal, PC enclosures). /s

This really wasn't meant to be so ranty, so my apologies. I think fondly of those days. I also tend to think about them a lot more when people say silly things like 'quality of software isn't what it used to be'. It really depends on what 'used to be' means. (-:

[0] Sure, complaining about an installer you run once is weak, but while I mentioned that big computer upgrade, I didn't mention was that it was funded by my father selling PCs which I assembled and configured DOS/Windows/Networking on (we had some corporate clients). It was a side business he set up as a way for me to make enough money to buy a top-of-the-line upgrade. I was 13, or so, and we were ... successful ... just my take in it paid for a car and a 486 that cost as much as a car. I installed ... a lot ... of DOS ... and Windows.

[1] If memory serves, it was actual Win32 API code that they had a license to from past contractual agreements (they still had to pay for the license for each version but they were legally allowed to include it on install media), so it wasn't so much a compatibility layer as it was ... Windows, running on OS/2 with stability as a future feature ... of Windows, and nearly every Windows app of the era. Later they removed the compatibility layer, and released a version where you could provide your Windows installation disks to get the compatibility layer. The two were meant to feel tightly glued together, but someone mixed up glue and lube.