This is a hard question. From what you say, you are trying to make a huge jump…. Great idea. But if you make it too long (like years) in between the purchase of one really great component and the rest. You have a couple other mediocre components bringing the overall performance down. … years go by with a very suboptimal system.
I am not ever in favor of changes in less than 2x investment. If you want to even up the performance on all components, you have to choose from:
Streamer, DAC, Preamp, and amp.
Typically if really well chosen they should all represent roughly equal investments. The Denon is an AV box… so ideally all of its functions should be replaced.
Assuming you are OK with your amp. Then focus on streamer, DAC, and preamp. Something like a Blusound streamer (or next step up… much better), a Schiit Yggdrasil DAC, and a used high quality preamp (audiophile quality… like Audio Research, Conrad Johnson, Cary or other). The preamp really sets the tone of the system. I think you could get all these for around the upgrade cost of one piece.
This would get you a huge upgrade… and a system you could live with for years while saving up for the next level.
There are a lot of ways to do this… but I don’t like getting caught with only one spectacular piece. Although, if I did… it would be the streamer (yes, the streamer… If I was going to pick one piece I would get an Aurender N10 streamer… but then throw in a Schiit Yggdrasil DAC (because this is an outstanding streamer… I know this is counter intuitive.
Well, hopefully my point is clear… it is a system and one or more suboptimal components makes for a very sub optimal system.