> in terms of security
I wouldn't go that far. As soon as you went online all bets were off.
In the 90s we had java applets, then flash, browsers would open local html files and read/write from c:, people were used to exchanging .exe files all the time and they'd open them without scrutiny (or warnings) and so on. It was not a good time for security.
Then dial-up was so finicky that you could literally disconnect someone by sending them a ping packet. Then came winXP, and blaster and its variants and all hell broke loose. Pre SP2 you could install a fresh version of XP and have it pwned inside 10 minutes if it was connected to a network.
Servers weren't any better, ssh exploits were all over the place (even The Matrix featured a real ssh exploit) and so on...
The only difference was that "the scene" was more about the thrill, the boasting, and learning and less about making a buck out of it. You'd see "x was here" or "owned by xxx" in page "defaces", instead of encrypting everything and asking for a reward.