1. At first I resented AirPods for not sealing out background noise, or fitting securely. But then I realized its a feature and not a bug. You can be in a private space while not fully disconnected from the public space. Just another tool in the arsenal
2. People have mentioned IEMs. If you feel discomfort from most headphones, you can get custom ear molds made for IEMs. In the US, this is generally a co-pay to an audiologist for a visit, around $50 for the audiologist to make the impressions, and around $100 for the custom plugs. IEM technology has not changed drastically, so you can buy used or older models. A 10 year old triple driver IEM will likely sound better than any non-IEM option. Make sure your IEM choice has detachable cables, as life happens. Plus, you can then use something like the FiiO UTWS1 to turn your IEMs into a more modern experience. There will be a downgrade in quality but it will be worth it for convenience.
3. Microsoft likely made a mistake with the size of these buds. They look like gauges that people put into their ears. This will either be a failure, or in the modern world of branding, an unlikely success.
FWIW, FiiO has cheap IEMs that are pretty good. For under $200 you can get a pair with 3 drivers in each ear (F9 Pro), and the aforementioned bluetooth “true wireless” adapter. Add another $200 and you have custom ear molds.