For an interesting example, check out this place: Google: https://www.google.com/maps/@46.4133003,-87.5248774,5345m/da... OSM: https://www.openstreetmap.org/#map=14/46.4161/-87.5406
Neither has the actual current lake boundaries (as used as a retention pond), Google has roads where the lake is while OSM doesn't, etc.
https://elevation.nationalmap.gov/arcgis/rest/services/3DEPE...
It's listed as a Theme Overlay at https://viewer.nationalmap.gov/services/
*in the US - it's a TIGER-specific thing (and certainly not exclusive to OSM). It doesn't affect the rest of the world.
Interested to learn what you're doing with cycling routes - I've been working on improving cycling directions in the US (for my site, cycle.travel) for a few years.
For cycling stuff I'm mostly ensuring that mountain bike-specific trails are in OSM and properly tagged (eg: highway=path and NOT highway=cycleway as some are wont to do), with appropriate intersection markers, names, etc.
My goal is to ensure that these trails are in OSM so they'll flow down to Garmin, Trailforks, Mapbox / Strava, etc. I also use the OSM data, exported to vectors, to make PDF maps to support the local trail advocacy/building org that I'm part of.
As examples, check out my edit history: https://www.openstreetmap.org/user/c0nsumer/history#map=7/44...
Here's examples of the print maps I've made. Versions of these hang at many trailheads in southeast Michigan:
1: http://www.cramba.org/storage/maps/stonycreek/CRAMBA_Stony_C...
2: http://www.cramba.org/storage/maps/pontiaclake/CRAMBA_Pontia...
3: http://www.cramba.org/storage/maps/riverbends/CRAMBA_River_B...
Print maps are made using osm2ai.pl to get the routes into Adobe Illustrator (AI) format. I then stylize things there. I know I could use GIS software, but QGIS is a pain to get things looking the way I want (similar to Michigan DNR maps) and ArcGIS is too expensive for unpaid volunteer work. It's also way more hand-off-able in AI format; I can send the files to any graphic designer and they can keep-on with it. GIS software requires far more specialized knowledge.
There's a number of us who use this kind of data for building back country cycling routes, and while it's great guidance, there's both the problem with roads being listed that are no longer passable (nor often even visible at ground level), or other routes available that don't exist.
Of course, this gets back to the way much of the data is crowd sourced... And we're working on that. :)