I think I am already in love with the way it is right now. Listening to ASMR videos which I recently stumbled upon amazes me. It is so lifelike if I close my eyes I feel like the person is actually beside me. A little creepy actually.
You should also follow the used listings here for DACs. I would say that expanding your budget responsibly on a DAC you will be pleased with is always worth considering as it can of course be used in both a speaker and headphone based system simultaneously so the investment has more ways to pay you back.
I had a nice Schiit Guingnir for 3 years (not the multi-bit) and quite liked it. Before that I used an Audiolab DAC. Since moving to the NAD M51 I am content for quite some time, and if it is another 3 years before I can afford to try a new sound signature I will be just fine. I would suggest you read up on the M51 and see if it catches your attention as it did mine. I have seen a few going used here very reasonably. The member who sold me his M51 to fund another more expensive DAC purchase let me know that within a few months time he went out and bought another M51 as he just missed the musicality of it.
Whatever you do, of course be responsible, but it is always cheaper in the mid/long run to spend more if it means getting what will please you. While experimenting is fun, if you buy and try several $300-$500 DACs, each time taking a little loss selling them only to arrive at the purchase of the $1500 DAC you really wanted you have killed off some money. Adain, for many people, including me, I have had to incrementally move to better gear, but if I wasn't in a tight financial position, and knowing that I will eventually invest the funds anyway, I say skip the entry level and buy sold mid-fi gear (or better if you can and want to do so).
While it isn't a straight relationship between cost and quality, there most certainly is more often than not a solid relationship. The most important thing is to know what attributes you most value, research the hell out of things, try before you buy if possible and then make the move you feel is right for you. Ultimately you always take a gamble, but with some research and common sense expectations the risk should be quite minimal. Good luck.