Unable to answer "How does this path cross the barrier here?" – node/9563640051 via StreetComplete 60.1:

Not a usual barrier?

Attached photo(s):
https://streetcomplete.app/p/258731.jpg

kissing gate and normal gate here

via StreetComplete 60.0

This is an overflow car par for Heads over Heels.

via StreetComplete 60.1

This is the main car park for Head over Heels.

via StreetComplete 60.1

In context of overlay "Addresses" – way/764010979 via StreetComplete 57.3:

Needs to be split. Right is Holly Cottage, left is Beechview Cottage.

There's a building here which looks like a garage.

via StreetComplete 57.3

In context of overlay "Addresses" – way/764010978 via StreetComplete 57.3:

There seems to be two addresses here. Stockton Cottage (left) and Elm Cottage (right?).

There's a slope and steps side by side. Steps have a hand rail on one side

via StreetComplete 57.2

Left: Lane End 4 and Right : Windyridge

via StreetComplete 57.3

In context of overlay "Addresses" – house name Rockcliffe: Semi-Detached House – way/763474159 via StreetComplete 57.3:

Left is wendholme right also starts with W but hard to decipher. Check with post codes.