To return to Joe's original insight -- why are some notes hard to match singing? -- I have the same problem (and pretty much of a tin ear; electronic tuners are a blessing), except reeds are for me the best instruments. I tried singing to match a note from a midi script, using the many instrument voices available, and the organ was the easiest. The theory that the harmonics match one's voice sounds good to me. I also find that when I try to learn a song from a recording, some people's voices are easier or harder to match. I've found that Garnet Rogers sounds great, but I can't sing along and find the tune.
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