Firstly, congratulations Erik on the new addition to the family!

Particle Build (IDE) support will be great to have when it's ready, but (correct me if I'm wrong!), I don't think that will mitigate the initial update problem, will it? The initial update will still need to be applied, and then it can be either Particle Build all the way, or Arduino IDE, or combination of both?
Now, T-Roy... I won't say it's simple... (after all there are multiple steps on the
wiki support page!!)... but I think it will be unavoidable, and you can play with the Oak using the Arduino IDE in the mean time if you wish. There are a couple of options - online update, local update, serial update. If you want to avoid the whole issues, you could just do the
serial update. However, I wouldn't do that until you have tried the initial online update at least twice, as it may just work for you. I found the
local update method fixed all of my over the air update issues, so never needed to resort to the serial update. However, I have seen mention of that failing for others, so it isn't foolproof!
Looking forward to seeing some cloud IDE support... will be sweet being able to code and program OTA without even needing to be at my own computer!