OpenStreetMaps is already excellent, but it seems like it could do with impetus in some areas. For what it's worth, these are some gaps that occur to me:
* Standardization of the model for mapping on multiple levels, and with 3D, and integration of that with the editors.
* Finding standardized ways to test, approve and automate maintenance of data consistency. There seems to be a lot of ad-hoc script editing, like someone writing a script to make a one-off edit of the global dataset to do a spelling correction. If that's going to happen, it should have pre-approval, and probably be integrated into an official, periodic checking and consistency process. Along the same lines, I'm not convinced small malicious or mistaken data edits will be picked up as quickly as they should be. I think most of the tools and structures are there to build the map, but not necessarily to maintain it.
* Doing more to link the OpenStreetMap.org site to the projects using the data. i.e. more clearly positioning the site as a data repository, and place to find ways to consume the data, and less as a toe-to-toe competitor to Google Maps.
* Pushing forward in links with wikipedia, preferably forming a connection with the structured/geographical data on wikipedia (if it's possible to find a license which is compatible with both projects, and wouldn't lock in either party). Having more eyes on the data should help to prevent bit rot.
* Finding hardware to automate data collection for Mapillary (the Streetview equivalent).
* Improvement of search/geocoding algorithms - to try to fill in patchy street data information (i.e. detecting sequences in house numbering). Then using those algorithms both to improve the geocoding capability, and to prioritize where data most needs to be collected - a handful of house numbers are vital for a major 5km road through the centre of a city, but they are far less important for a 30m cul-de-sac.
* Finding ways to have more area based mapping for pavements, cycleways, shared space roads, pedestrian crossings, public squares etc, as an additional, progressive enhancement to the line and dot model for footways, highways, etc. Something which can be used to provide additional information in city areas where that sort of low-level mapping is useful/necessary, but isn't necessary elsewhere (clearly the whole world will never be mapped in the detail that you'd like to map central London, or one particular central railway station)
In general, trying to develop policies to encourage the database to be maintained, and data collection to be managed, in a way which makes it easy to consume the data in a structured way.
Glad to be corrected if I'm wrong, or ignorant of progress.