I think B2B software should be able to create manageable installations for technically competent IT professionals..
If your install has that long of a manual task list, your cloud SaaS infra is probably junk too.
Back then, learning how to manage your own PC and install software was tantamount to earning an IT certificate. Doing so for a few years in high school would be enough to qualify you for a career in IT.
So I politely disagree. The industry was never able to ship software that a non-technical person could install. Especially not B2B, but barely B2C as well.
In the very early 1990s, something like "Insert disk 1 and click the disk icon, then click <name of application>". Installation to the hard disk was optional, and might be one or two steps.
Later in the 1990s, installation was pressing "Next", "Next", "Next" after inserting the CD.
Software has to handle much more hostile environments.
Perhaps not thinking of a "time when", perhaps thinking of an OS that required an IT certificate.
Because even early Macintosh System Software (classic Mac OS before OS X) was bewildering to Windows users, since any user could "drag" a program from a floppy disk onto their hard disk, leave it anywhere, and it worked.
Arguably, OS X introduced the Applications folder in 2001 partly to give people a place to drag things to and feel more comfortable that's where they could find their "Program Files" (but mostly so multi-user system users would get to add and re-use apps in a common clear place they "should" be).
But you still didn't need an IT admin.
Installing software means clicking the button, waiting, clicking yes on some permission prompts, and logging in with Google.
The only thing about any other software I can think of, that would be inherently any harder, is if it involves domain names and certificates. Which is a problem we should be working to solve, and I'm still annoyed at Mozilla for cancelling FlyWeb.
Unless you're such a big company you can definitely afford IT staff, you're probably not doing anything that needs separate services or a database or anything beyond one executable with SQLite, same as consumer apps.
Mac OS X Server?
The vast vast majority of SaaS products talked about on HN are probably not even 1/10th as complex.
"But we want it to integrate with our single-sign on product."
"Our security team scanned it with our chosen tools and you have to fix these things before we will deploy it."
"We aren't willing to make those network changes to allow it to run."
"We won't allow it to connect to our <foobar> server but it is a requirement to connect to our <foobar> server if it is going to be hosted internally."
This is the stuff that makes "enterprise" deployments difficult. Oh and they want you to hold their hand through it but they aren't willing to pay for consulting.
These sound like tire kickers and un-serious customers, why focus on their expectations?
Serious customers, almost by definition, are willing to pay for custom work they want done.