Two Start / End Points on Same Route (not split)

Not yet, but this feature is on the wishlist of many users.
Straight-Line / Point Planning mode / Plotting a track on unsurfaced roads

It should not be added to the open source map as there is a barricade restricting car access.

IMHO this bridge should definitely be added to OpenStreetMap, as well as the barricade.
If there are any restrictions, this information can (and should) be added as tags.
See FAQ to OSM

Manfred

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