Throughout my life, things have always gotten worse.
I've come to the conclusion that for any major investment, the time to invest was the early 2000s, and the second best time is right now, because it's only going downhill from here.
Unless it's tech, because early tech is almost always shit compared to later versions of the same... To a limited degree. Eventually it all gets enshittified.
I never knew someone with an analog cellphone at the time, so that one isn't something I experienced. I was one of the first at my high school to have a PCS phone, and I remember that not all PCS phones could text.
Depending on what tech the carrier used, you either could text, or not. GSM phones came with the feature as standard, while CDMA and TDMA phones were distinctly lacking the feature for a long time. It's funny to me that the feature that made cellphones really explode with the younger generation (texting, aka SMS), wasn't even a universal feature when the PCS networks went live. Eventually we all switched to HSDPA, and eventually LTE which both had the feature.
Aah those were the days. Everything was slow and it was still great because the alternative was nothing.