Acknowledgement and work on these issues is happening both on github.com/digistump/OakCore and on Kickstarter updates.
You can't connect an Oak to a USB port - as we've tried to make clear from the very start, it is an OTA only device, USB is power only. You can use a USB to Serial adapter to load things on to it (it works!), but that of course isn't the main goal. As far as Particle.io being the only way - you can also use a serial adapter, you can use a local particle server, or you can use your own custom update firmware. That said, the particle updates are working for everyone who has got that far, it is the initial update from our servers (not Particle) which comes to the Oak over HTTPS that isn't working for some.
As far as how to update with a usb to serial adapter - the reason for putting the Beta out there is to get feedback on the update process and firmware, if we opened that up right at the start then we would not have gotten much feedback that we need to solve these issues. Not to mention my focus has been on solving the issues as best I could first. We'll be releasing the bin file to update to the latest firmware along with the first non-beta firmware release, if nto sooner (as soon as I get a chance). You can build it form the OakSystem repo already.
-- while I was writing this tcarleton posted their message---
I'm not convinced it is a router issue either, not convinced either way, as I'm still only able to reproduce the issue very sporadically - and I'm working on some firmware that people with serial adapters that are having issues can run, and it will generate a better log to serial that might help discover what is wrong. I suspect it may have to do with connection speed/router speed/basically how quickly the data is being thrown at the Oak.
Everything is SoftAP is minified and pulled into a single file because your browser needs to have that whole file in memory, since you disconnect from your internet during the process. It has little to do with the update process, other than the wifi connection itself, if you watch the network inspection tab you'll see the Oak just gets your wifi connection data from setup, this triggers a restart to the update rom and that downloads the update from digistump's servers - the Oak doesn't get the update from Particle. That said, you can find all of the sources for the included js on particle's github (github.com/spark) in the SparkJS/ParticleJS project and the softap-setup-js repos - we should pull those all into sources file in our repo in the future.