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Musiciano may be right honestly, both in a practical sense, and a more figurative one. It is really tough making inferences on vocal qualities without sound. But also, you really just have to try going higher on your own. Sometimes progress is constant but slow and gradual, others you may seem to go nowhere for months, then suddenly be able to reach whole new boundaries, like SHAZAM! =P

But yea, it seems a bit odd to me that you are breaking into falsetto with the nay sounds. Are you sure you are using the "whiny" sound well enough for that excercize? I believe that though it's somewhat of a "bad" coordination, it's meant to help connect your bridge. But then again, A is above first bridge(not sure where the other ones are :P), which is why I'm not quite sure what to say about what to do. As such, the best I feel I can say is to experiment, so long as you are hurting yourself. If it happens once or twice its fine, but don't overexert yourself. Try experimenting with dopey sounds(not overly dopey, that will probably cause you to crack a lot), work on nays more, lip rolls, tounge trills, etc.

Part of the problem for assessing this issue is that I also don't know what exactly you want to move up in, with what sounds you want to go up. For example, there is a difference between trying to move up in "raw" range, as in the highest note you can reproduce regardless of tonality. Like, the highest I generally seem to be able go at all right now is a G above high C, using a loud edgy/cryish sound. Sometimes higher or lower, but generally around there. With lip rolls and toungue Trills, generally I top out about E above High C. My regular head voice seems to top around D5. I can't go anywhere above B flat below High C in a mix though, and barely at that. So yea, it depends on what exercises you are doing.

What do you think you are doing? Without sound, I'm going to need the best description possible. Are you straining or tensing alot before it goes breathy? Are you doing the excercizes really lightly? Which exercises specifically are you having the most trouble with? Also, by exercise CD3, do you mean the very first CD with exercises? Sorry, I'm not sure because I ripped all my SS CDs onto my PC for convenience.

The way I see it personally is as follows: you should always be pushing yourself to an extent. Generally, if you aren't striving for more, you won't get more. Go to your limit everytime without hurting yourself, then push yourself to go a bit higher. There'll probably be frustrations and dissapointments along the way, but that's the way the journey is :P, its worth it =]

Also, as musiciano so wisely advised, don't be afraid to crack! sure, that's what you're trying to prevent, but don't be afraid of it you know? The vocalizing and excercizing will wear the cracks away, a river polishing the stones of the voice(yay corny metaphor!). It's understandable that you wanna get rid of the cracks when singing, but its ok to crack when you're vocalizing, unless like that excerize is meant specifically to prevent cracking :P

As a note though, if you connect headphones into a microphone port, they will actually become a microphone. Different heaphones will give you different results though, some might be too low in volume =P. Usually, the larger, the better the pickup. Either way, I recommend you get a mic, it's a really worthwhile investment!