I understand where the OP is coming from. I too enjoy the sound of my computer speakers, Logitech Z-5500. They have the most open sound of course compared to headphones, they have a very nice bass rumble and music sounds great with them. But I also have expensive headphones and a nice DAC and Amp. I think it’s ok to enjoy both. You might have a tendency to lean towards one over the other depending on the context. There is no right or wrong, good or bad. It’s totally subjective and based on personal preference. Enjoy what you have and save for what you don’t and really want.

I’ve got two. Topping D90SE and R2R Denafrips Ares II. They both offer me options when listening and varying experience whilst listening. Topping gives me Bluetooth option to connect, so I can stream Apple Music from my phone, or other streaming services or YouYube. I’ve really utilised this feature, so useful. A great DAC IMHO, and is a very resolving and clear sounding DAC. The Ares II gives me a slightly less fatiguing listen, with more spaciousness and smoothness. Perhaps slightly less detailed than the Topping, but so minuscule a difference. I enjoy both. I bought DACS only, so could pair with different amps. Balanced connectors for everything. That’s my input.

No regrets. Chalk it up as the cost of enjoying a hobby, which brings excitement and requires building your knowledge. If you have cans you don’t use as much anymore, sell them second hand and use the proceeds towards new gear. As we are all on different stages of the audio hobby progression, beginners can get into the hobby by buying well cared for gear at a fraction of the new price. I think cans are just one part of the bigger hobby picture. DACs, amps and music library also provide a source of technical learning and appreciation. The question is, what would you have spent your money on otherwise? If the answer is alcohol, drugs or partying, I’d say spending your money on audio has been a wise choice (haha).