What I remember most about the World Wide Web from 1994 thru about 1998 was the persistent need to keep changing dial-up ISPs once your trial period ran out, anywhere from 14-days to, eventually, 3 months. You only had so many included hours per month, then you'd get billed by the minute or hour for uptime. I ran through about a dozen ISPs during this period. I remember first signing up with an outfit called GNN in mid-1994; it was later acquired by AOL.
Another thing I recall from this period was needing to jot down all the international ISP dial-up numbers which had an agreement with your ISP. This was needed when travelling outside North America, that is, if you wanted to connect your computer remotely.
The last annoyance I recall was the early cell phone days. Most cell phones had adaptors to connect to your laptop's PCMCIA card. Often you had to use a PCMCIA "cell modem" to connect to your cell phone. I think I also had one phone which connected via a PCMCIA serial port card. I don't recall ever getting more than 1200 or 2400 baud using the cell phone. It was mostly good for checking e-mails and talking rubbish on IRC. I used an LG Phenom Express from (I think) 1998 to 2005. https://www.pencomputing.com/showcase/lg_phenom_express.html Remember handheld PC's?
Some random memories from pre-2000, in no particular order:
I was a strong user of the hotbot search engine.
I miss the sounds emitted when connecting through a dial-up modem.
I do not miss having the internet disconnect when a phone call came in. It didn't take me long to order a second phone line just for the internet.
I miss the novelty of 1990's internet and its simplicity. If I was given 10 years left to live and was given the opportunity to go back to any 10-year period of time I had already lived, it would probably be 1990-2000.
I'm still on IRC and never took a break from it. It's an idler's paradise now, but I do find people from 25 years ago coming back to it again. I remember when I was learning programming, the guys on the C channel were quite helpful.
My favourite ISP of the time was CompuServe.
I remember most libraries had a dial-up service to search their catalogues. My memory is a bit foggy, but I think we used HyperTerminal to log in there, normally at 9600 or 14400 baud.
Before mainstream internet, we used dial-in BBS services as a newsgroup and a place to download firmware or BIOS updates.
I didn't have DSL until around 2001 and the lousy phone lines in my ancient apartment building never let me connect at more than 26400 baud. Even when I had DSL, it as very slow, about 128K max.
Napster and Bearshare remind me of early DSL days. ICQ reminds me of the dial-up days.
I remember there being some rather sleezy Macromedia Flash games. I specifically recall one related to condums.
I enjoyed experimenting with shareware from Tucows.
I do not miss the noise those early Ultra2-LVD SCSI drives made, even when brand new. I didn't measure the dB, but it felt up to 10x louder than ordinary IDE drives of the time (both the platter spin noise and the read/write head noise). The noise would sometimes wake me up.
That's all I can think of for now.
Plan your life wisely, you'll be dead before you know it.