I also had an ipaq ~2003. It didn't have enough storage to be a reasonable music or movie player for commutes and (mine anyways) only had wifi via a honking PC

I also had an ipaq ~2003. It didn't have enough storage to be a reasonable music or movie player for commutes and (mine anyways) only had wifi via a honking PCMCIA adapter that drained the battery in no time, so I otherwise browsed the web with a laptop. No websites were anywhere near designed for small screens in those days, either. You're right that the OS was garbage, further limiting the already limited hardware. I think I also got linux or BSD running and messed around with some WEP cracking in my neighbourhood for a bit, but then it otherwise sat in a drawer. I was still in school and it was a stupid and expensive purchase, but it did teach me to only get new tech if it was actually useful and otherwise wait, which as served me well since, including the iphone (which the first one was barely adequate for what it promised).