Hi,
First of all thank you for sharing your point of view. I found myself in a similar situation, however with the Particle Cloud instability issues and some other limitations on specific stuff I was doing (MQTT over SSL) I ended up trying out the ESP8266 Arduino solution on the Oak.
Pleased as I am with it - even the OTA update mechanism seems robust enough - how would you say the Oak fairs against an ESP8266-12 + IO Adapter Plate Expansion, considering the use of the ESP8266 Arduino firmware on both?
(see image in attach for a clearer view of what I mean by ESP8266-12 + IO Adapter Plate Expansion)
The ESP8266-12 doesn't have the micro-usb port for power, however it is significantly cheaper than the Oak. On the other hand, maybe the Oak has better electronics circuitry than the ESP8266-12 with the IO adapter plate - something I know nothing about since electronics is not my background.
I'm considering this comparison because comparing the ESP8266-12 alone against the equivalent Acorn by Digistump does little for development in terms of accessibility over pins and power, on this particular thread discussion.
All that said, my point is, if using the ESP8266 Arduino firmware, would the Oak still have advantages over the generic ESP8266-12?
As for the points you've mentioned, I'd just like to mention that to me:
4) in the cons section shouldn't actually count as it was your decision to do it I guess, whereas you could have just work with one module first and then broaden the setup to a few more modules later on, like some people do, me included.
By then perhaps you would have realized if soldering female headers was the way to go or not for whatever project you were working on, before doing it to all the modules.
The same should be said about OTA updating: regardless of the infrastructure used, update the production line only after lengthy and successful testing with the development units and do the production updates in a phased manner, splitting the production range into several groups.
As for point 5), I'm not sure I understood it correctly, but you can always solder the pins the other way around and even remove them later on, if you don't want to use them. Both pin headers and Oak or ESP modules should be re-usable, it just boils down to soldering skills and not the module architecture/design, in my opinion, having done that myself.
Again, should not be seen as a specific limitation on the Oak board itself.