Help with DAP Upgrade?

Hi All,
Not really sure what catagory this belongs in, but here goes. I find myself using my portable rig more these days, just fits into my lifestyle better. I currently have a Hiby R3 Saber Pro, TIN T2, Moondrop Aria & Reacho & Peacock Spring. Thinking about an upgrade, and have about $500 to spend. My immediate thought was to upgrade the DAP to a Cayin N3Pro. I like tube equipment, and am familiar with the sound. Do you think this is a significant upgrade, or should I just save up for an N6ii or DX300? Also, would I be better served at this point putting the 500 into a new pair of IEM’s with my current source? Decisions, what do all of you think?

Have you looked at the hiby R5 since you have experience with them and…1w balanced is real nice.