I've been a developer for just over 10 years now, and I would say the opposite for myself. 10 years ago, I would never have written a response like this. Now, I would in a heartbeat.
I do think that he will find it embarrassing in 10 years, but for different reasons (like in 10 years, Windows is a super awesome development platform, or running on Amazon Web Services is like running on IIS, or jQuery is the new VBScript, or something like that).
Except for one big difference -- today, I or the company I work for, doesn't have to own "the mainframe". Basically its a return to the "mainframe" with the cost and exclusivity. That is a huge difference.
In the 70s you had "computer bureaus" that owned the mainframe that you would rent time on by the hour. A lot of the early MUDs ran in spare capacity on these. Exactly like the cloud...
I do think that he will find it embarrassing in 10 years, but for different reasons (like in 10 years, Windows is a super awesome development platform, or running on Amazon Web Services is like running on IIS, or jQuery is the new VBScript, or something like that).