So - definitely at least season 1 of Legends of Tomorrow Len, and post the Chronos reveal, but how much further along?
The Waverider never visited Siberia in 1892. I don’t even think it had the time in season 1 for that after the Chronos reveal.
There’s the whole “there are no strings on me”. Which could be foreshadowing of Len’s personal timeline or it could be Len making a callback to the Oculus. Can’t tell.
So - either post!Oculus Len or sloppy writing?
I don’t understand why there was no Mick, though (apart from Dominic Purcell probably not having been available) - though I suppose the third option is the brief time period between the Chronos reveal and Len and Mick’s heart to heart - except they seem to head straight to 2147 after picking up Sara and it’s at the end of that episode that the heart to heart occurs. And after that Len carries bruises for several episodes, so - no. Does not work.
I really wish it was Oculus!Len, but realistically - probably sloppy writing.