Make sure there’s no lint and dust compacted in the bottom of the port if you haven’t already. It isn’t always entirely obvious but it can affect both lightning and USB-C and you can usually get it out with some careful use of a sewing needle.
I’m definitely going to be an outlier here, but I still use an ipod nano for my day to day podcast listening while commuting. But sometimes if love to be able to just unplug my earpods from my nano and plug it into my phone to watch a video or something. Can’t do that now unless I dig into my bag for a dongle.
I’m absolutely still using teamspeak. Nice and light, and it let’s us run a soundboard plugin that let’s you have unlimited length audio clips. I just wish they’d update the plugin to support the 64-bit version.