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Here's what I think will solve my problem:

I want to be able to sing and hit notes. I'd like a program (for almost any platform; in order of preference, Mac OS X, Android, iOS, Windows, Linux) that plays a note as a sustained tone and listens to me as I try to sing the note and hit the right pitch, graphically showing if I'm too high or too low.

My problem:

I'd like to learn to play an instrument by ear. In finding out how to do it, it is important to be able to replay the song in your mind and tell if you are hitting the right notes, and it helps if you can hum, whistle, or sing it. I can't sing on key, and I can't whistle. Perhaps this is why the whole idea of 'auralizing' (imaging a sound in ones mind) seems strange to me. In any event, starting where I'm at, I think the best step to learning to play by ear is learning to hear if/when I hit a note.

Bonus/secondary feature:

It'd be nice if the application also had a mode wherein it would playback a song, at different rates, and let me try to hit the notes and show me how I'm doing.

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To start off: I don't have a software recommendation to a program which plays a tone, and listen to you reproducing it directly. I have however three suggestions which might help you

SingStar or similar program

For the Playstation there exists a game called SingStar, where you are supposed to sing along and it will give you a visual feedback to whether you hit the notes or not. Similar games is available for all major gaming platforms. This could somewhat help/train you to get the pitch correct.

Learn music theory and especially chord theory

Playing by ear takes practice, and lots of practice. It doesn't entirely depend on being able to 'auralizing', but it also comes down to theory. To a lucky few they are able to do this without thinking, but for some of us training is the key...

To help you on the way you can start learning to play an instrument like the piano (which doesn't need tuning! :-) ) and learn to play chords. Then you can learn the theory related to chord progression, and when practising this for a while you'll get used to what is 'correct' and 'not correct' for different styles of music.

After some time doing this, you'll (hopefully) will find it easier and easier to use the 'correct' chords, and be able to pick chords for songs and make/change arrangements of your own.

Get vocal training

There is a slight possiblity that you are tone deaf, as there is a low percentage of humans which actually are that. If you get vocal training you can ask for this, and if you are not tone deaf they'll tell you and can help you be more proficient in learning to hear and correct your pitch whilst singing.

If not tone deaf, you could/should also consider joining a choir at some time in your training to get further help and guidance on your way.

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