Hi - I'm pleased to say that you can already upload photos to share with your routes. This facility was introduced in the latest upgrade to the site which we released a couple of weeks ago. You can upload photos in the route planner - click the PHOTOS option in the action panel in the bottom right corner of the map. You can also locate photos on the map if you like, with clickable icons, and add captions.
This is an example of a route with photos: Kilimanjaro Machame Route
John
I have requested this a long time ago so will request again if pictures can be uploaded to give a better idea on what to expect on the walk! Sometimes going to new challenging trails you need a good pictures to show if you can do the walk.