I'm with you, but I started to make inroads into digital pretty early on, around when home theatre surround sound became a thing. I got a JVC 5.1 home theatre audio system, and picked up an add-on for my sound blaster which added optical output, and plugged that into my JVC, so I could get 5.1 surround while watching DVDs on my 25" CRT.... I think it was 25? 1600x1200. I remember that much about it.

I still have, and use, my JVC. On my PC, I've gone a bit more audiophile than what most people do. My desktop system doesn't have any audio on board, so I picked up a Yamaha USB mixer. It acts as an audio interface (headphone out/mic in) for my system, and I use analog wired headphones for it.

My cellphone doesn't have a headphone jack anymore, and neither did the last one. So it's been about 6 years since I had a headphone jack on my phone. When I first got a phone without a headphone jack, I found a Bluetooth device that's essentially just a headphone jack. The one I have is "premium" and not the cheapest, it's a Fiio BTR5. I have a small set of headphones for use at home and on the go. For home I'm mainly using a pair of Sennheiser HD 598, which I've had for years, and on the go, I use mainly IEM style earbuds, usually moondrop starfield, but I have a couple other pairs. I still have my old speakers and sub that I used on my PC for a while, but I don't have them set up. They don't sound very good, and my headphones are comfortable enough that I prefer them anyways. When I'm on my computer, I usually don't want to broadcast the sounds from my games and such to anyone else, and the Mrs works afternoons, so I would disturb her if I used them often.

The JVC is now being used for my TV, still over an optical connection from my TV. It still sounds great and I'm still using the original speakers for them.

I like telling anyone who will listen about my Fiio, since, even if they don't buy one because of the cost, there's inexpensive alternatives, even some from Fiio like the BTR3, which will help beloved headphones out of the landfills, and keep people from buying Bluetooth devices that are going to fail within a few years. I've had my Fiio for 5+ years and I'm always looking for reasons to use it. The nice thing about it is that it can operate in USB mode (no Bluetooth) and it can also charge while it's being used. That's more than I can say for almost all Bluetooth headphones on the market, especially the airpod style ones, which need to be returned to their carrying case to charge. Other Bluetooth headphones generally turn off when you plug them in to charge, even if the charging port is able to be connected while you're wearing them. Some newer units can do this, but it's still fairly rare. So I use my Fiio with my phone on the go, with my PC at home and at work when I want to listen to music.... It's pretty handy. No USB drivers are needed, so just plug it in and use it in USB mode, which makes my boss and IT guy happy, since I don't need to be an admin to get it working.

Anyways, enough from me. I just wanted to share my experience and thoughts on it. Hopefully this gives you (and others) some options when the wireless revolution forces you to seek alternatives.