Bose cans are moddable. In the case of the Bose On-Ear, I would perform surgery on those bean bag cushions with the pee-hole sound outlets. If you open these up, you'll sacrifice bass to get a more open presentation. Since the Bose On-Ears have ridiculously bloated bass, that would be no sacrifice at all.
As far as the Triports are concerned, the most obvious problem is the acoustic silliness of putting drivers into aviation cups with inadequate sound damping. Those aviation cups are too small. With no vents and no serious damping, it's like listening to music inside a literal can. Bose can't open these up without sacrificing its chief marketing angle: isolation. The size of the cups aggravates the problem. Bose doesn't seem to care, as long as it makes a product that looks good to consumers. Its "research" probably tells it that customers want the isolation suggested in an aviation-cup design but they also want something sleek, with a low profile. The cups are small to be cute and make the sale, not to provide the customer the best possible sound.
I actually owned a pair of Bose In-Ear Phones, for at least as long as it took to remove them from the package, listen to their awful presentation and head back to the Best Buy that sold them to me. When I returned them, I explained that these were possibly the worst in-ear phones I had ever heard. I was being nice. Bose's problem may have been another case of style over substance. If Best Buy is selling these for $99, Bose must be unloading them for much less. I'm sure these plastic nightmares don't get stocked unless the margins make them worth the store space. That being the case, Bose doesn't have the same cost-in-materials of any major player in the world of IEMs. Nor is the ear canal much of a location for expansion of the Bose philosophy of psychoacoustics. If Bose thought it were, it would probably have multiple drivers firing off multiple signals all over the place to confuse the brain into processing all these bizarre signals into some kind of artificial spatiality.
Bose's room units operate on such principles, which is how Bose gets away with selling a truckload of paper-cone drivers to create the kind of spatiality simulated with a comb filter (where notch filters cancel out frequencies A,C,E,G on the left and frequencies B,D,F,H on the right - to give the illusion that two separate signals are being heard, because the two channels fit like puzzle pieces). But you can't do that if all you're supplying is a single driver - a dynamic - in each ear. Dynamics tend to be bigger and have fitness issues. Their saving graces are soundstage and bass. Mine were boomy and muddy - with such a lack of clarity I couldn't explain why I'd paid $100 for the experience. They reminded me of Koss's $5 headphones at Walmart. Without a doubt, Bose supplies these to fit a market niche. Maybe that's why, in the years since I bought that rotten pair, I've not seen Bose come out with a single innovation in its in-ear phones. We've seen new products from UE, Westone, Phonak, JH Audio, Audio Technica, Etymotics, Sennheiser and even Klipsch. Bose, on the other hand, seems frozen in time. I suspect it's because Bose's heart is really not in the IEM game. Bose just wants to have a product to fill a niche. It doesn't care whether its product is even remotely competitive.
Bose makes cheap stuff you can sell at a mall, or a Best Buy or a Target, etc. The general public isn't that into headphones. Many of these people can't hear the difference, anyway. They just want something to plug into their Nano or Zune. They are Bose's bread and butter. Bose makes its cash by knowing the limits of their pocketbook, which is why it has products to fit certain low-end tiers. What's more, to get these people to spend more - in what is essentially a race to the bottom - it tells them how discriminating they are, since they spent a little more to get "the best."
Here is where I think any attempt to mod a Bose product will run into problems. The people who buy Bose believe, or want to believe, that the world is simple. They like it simple. They are buying a lifestyle product that has everything figured out for them. When, therefore, someone comes along and tells them this or that could be tweaked, it's not exactly a message they want to hear. Not only do they fail to appreciate the help (sometimes unable to hear the difference, anyway) but they actually feel like their little bubble has been popped. They had perfection incarnate. Then you showed up and ruined it. You introduced complexity. You showed them that their headphones are not made with unicorn tears and white magic. You reminded them that everything works because of things we usually don't see, but which are extremely important - and complicated.
You might as well have sung to them in Ugaritic.
If you managed to sustain their attention long enough to show them that their headphone is actually a system, with parts working together as a whole - and then showed them that their system needed this tweak or that - their attitude would now be one of dismay. Why? Because simple people have little tolerance for shades of gray. It's either good or bad, right or wrong, worth having or worth replacing. When you find fault with a lifestyle product, panic ensues. The reaction is either denial or disillusionment.
Take, for example the brouhaha over Apple's iPhone 4. In many ways, this is an awesome new phone, the best Apple has ever made, but is it perfect? As with any device, it's a little buggy. There's a tender spot where a left-handed user would short out the antenna. This is because the antenna is on the outside of the phone, wrapping around its sides like a snake. Antennas, like other electrical appliances, have positive and negative sides, which you don't want to cross. If a person were to bridge the gap separating the two ends of the antenna, it would cancel things out and the signal strength would drop dramatically. As AT&T has a service prone to such problems, the iPhone 4 has had issues with dropped calls.
Immediately, such news brought dual orthodoxies into an immediate collision. On the one hand, there were those who said the iPhone 4 was defective crap and should be immediately chucked, even if a host of right-handers didn't have any issues with it and if one could fix the problem by simply not giving the phone a kind of "death grip," as it is a device whose antenna would work better without being covered up. On the other hand, there were the iNuts, going into hysterics to defend the sanctity of a consumer product. Bitter diatribes were launched against YouTube videos where the iPhone 4's deathgrip issue was displayed. This was before Steve Jobs gave his Friday speech, basically saying that the other cell phones have their own death grip. After the speech, when YouTube videos switched - from Jobs' list of 3 less-than-latest-release phones to the 7 top-of-the-line/latest-technology contenders - Apple true believers became incensed when it was shown that the real problems were coming from Apple and Samsung.
Now, for most users, the "death grip" isn't an issue. For the left-handers, a strip of Scotch tape would do the trick, and that's if they didn't want to simply watch where they held the phone (since the divider between the two sides of the antenna is pretty hard to miss). But for the extremely simple, this was either a non-event or a deal-killer. Not only can't you tweak a "perfect phone"; you shouldn't have to. Simple people don't like to be reminded that the world is far from simple. Bose makes its money off such people, which is why I doubt they'll be receptive to a lesson in practical acoustics.