My last DAP is a Sony A35 with a firmware mod and with the unlocked amplifier flag but I rarely use it these days. Make no mistake that thing sounds wonderful and I actually use it on my desktop rig everytime I want to play meme high resolution songs. The modded firmware also lets me use it as a Bluetooth receiver/DAC, but I rarely do it. With that out of the way, I think a DAP is only worth it if you have IEMs or headphones that can take the full potential from it. Imo usually stuff way above 300USD. If you listen to music from streaming services (lossless or not) just take the money you would spend on the DAP and buy a better smartphone that can be used with a simple passive USB C to 3.5mm adaptor, or if you enjoy dongles get a simple DAC. So my answer is not worth it unless you have really great IEMs. (Edit for grammar)
My dad is recovering from cancer and it was a hard fight, I sincerely wish the best for Stallman.