Latency is a far worse problem with headphones than most people realize. A cheap analog mixer combining the DAW playback with a live feed split from a microphone or instrument can improve performance and speed up the recording process dramatically over even the lowest latency DAW. It’s less convenient but the results are well worth it in my experience.
Ironically, recording to a loudspeaker rather than with headphones is another way to solve the problem. I suspect the headphone issue has more to do with the acoustical sound mixing with the short delay from the digital audio than a longer delay from a speaker. Perhaps increasing the latency a bit is another solution.