Worst experience ever...
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If you claim this is the "worst experience ever" I guess you haven't used Kickstarter before. Personally I have to say I'm rather pleased with the hardware quality of the LoPy and these teething problems should be expected with any Kickstarter project.
To put your LoPy into the expansion board just check that the GND pin labelled on the back of the module goes into the GND socket on the expansion board, everything else will match up.
There are known problems with the firmware updater and we've been discussing workarounds in this post.
If you're looking for something that works out of the box, has gone through months of QA testing and has decent documentation I suggest you buy something from a large company like Apple, Microsoft, HP etc and stay away from community projects funded through Kickstarter. Or put your LoPy back into the box and come back to it in 6 - 8 weeks when the initial issues have been fixed and the documentation has been updated with all the possible problems you never see during pre-launch testing.
Arduino had the same issues when it first came out. The fact that the Arduino UNO now works pretty much out of the box and has decent documentation is because it's been around for many years.
The WiPy 1 which I also got through Kickstarter had similar issues when it launched but PyCom has done a wonderful job since then getting the documentation updated and continually improving the firmware.
I've backed other projects on Kickstarter that went dead pretty much as soon as the hardware was sent out. The miniSpartan6+ from Scarab Hardware is probably one of the worst examples.