What is the provenance of the source material? Was it digitally recorded at 24 bit/192 kHz? Some material which is labeled "hi res" is actually creating using lower resolution masters so their resolution is over stated. True hi-res tracks (such as those by Blue Coast records
https://bluecoastrecords.com are expensive. This is changing with Tidal streaming MQA and Qobuz (which is just entering the U.S. market - maybe is available in Italy?). Let's not get into an MQA discussion.
Assuming that you want to maximize the sound quality/Euro ratio, I would
1. Get the best headphones that you can afford. Put most of your money there. There are obviously issues using headphones vs speakers, but if headphones meet your needs you get better bang for the buck. Just be aware that identically priced headphones may sound very different, as one might be tuned for pounding bass, another might be mellow, another might be tuned for totally balanced sound. I have gone through a lot of headphones (Bose, Sennheiser, multiple Grados, Oppo, Etymotic, ...) and they are all different. Ideally you can listen to some of your source material via various headphones before you make a decision. That's very difficult here in the U.S. There is a thread on MacRumors where a whole bunch of headphones were purchased and compared.
This guy has been professionally evaluating headphones in major publications for decades:
https://www.cnet.com/pictures/wowza-the-audiophiliac-picks-the-best-headphones-from-26-to-6000/
2. Just get a simple USB DAC, such as the Meridian Explorer, AudioQuest Dragonfly Red, or something similar. As funds become available then you can see if more expensive DAC's are worth it.
3. Speakers, room treatments can then follow as funds become available. You will also know what sound you are looking for and choose speakers accordingly. My speaker criteria, for example, was to duplicate the sound that I hear at performances at my local concert hall. Took a long time to accumulate the cash to purchase them (Goldenears), but they are well worth the $ and the years I spent finding the sound I wanted.