my experience with gen 1 has been it's great under clear skies with moonlight, skyglow, light pollution.
You must go active when it's overcast, black skies or under dim starlight.
Even gen 2 will eventually require a illuminator when it gets dark enough.
Gen 3 will require a illuminator in a building with no light or really dark nights with very little natural light ( Think Afghanistan during a sandstorm).
The newer production gen 1 tubes are lower distortion than the older models. Light amplification is improved but nowhere near a gen 2.
My experience with gen 1 has been with Military units, NSPU 1PN34 Cascade scope (PVS-2 equv) and PNV-57E driver googles (They flew Mi17s with this shit in Afghanistan)
My gen 1's rarely struggle in urban conditions unless it's a thunderstorm and the sky is very dark. You gotta get out pretty far to see what a nightvision unit is capable of (Away from any urban light pollution)
My experience with Gen 2 has been D300MS (PVS-5 equv) GSCI Gen 2 scope (PVS-4 equv)
working on the gen 3 stuff