There will always be people who think crowd-sourcing or open-source projects are completely incapable of producing accurate, up-to-date or "complete" datasets/software because they have no understanding of the motivation, methodology or altruism behind such projects. Mr Ross seems to think all we do is plot lampposts, benches and bins on existing maps (and that Wikipedia is just "Family Guy" or "Pokemon" trivia). That's OK, let them pay thousands of dollars for their "professional" map updates, or have licences pulled out from under them a la Nav4All - blasting rebuttals at these people won't convince them, but making the OSM dataset the most cost-effective and comprehensive one available will make it unavoidable as a viable option from both a business and consumer standpoint.

Probably Track 'n Trail which can upload GPS tracks directly to OSM. I would love to see an OSM app on the iPhone but Apple would probably reject it for duplicating the functionality of the inbuilt Google Maps application.