I've not see http://www.wemakemaps.com/ before, looks like a cool site, but whats with consistently referring to OpenStreetMap as OpenMap? and how about adding proper attribution on the OSM maps?
I've been working on a watch app(Gaia GPS https://www.gaiagps.com/) and went to one of the labs to test it a few weeks ago. I dont't think I could have shipped a really useable app without testing on actual hardware. There was nothing majorly different from the simulator, just lots of minor things.
I found the API easy to use, it made for quick development due to the limited scope of what can be done. It seemed like if there isn't an obvious way to do something Apple doesn't want it done.