N1
たら〜で
Even if, If
ニートになったらなったで大変だと思うよ。
Even if you become a NEET, I think it would still be tough.
Explanation
「たら〜で」 has 2 uses
1If so, so be it
AたらAたで: even if it happens, you can deal with it, so no need to worry.
「もし失敗したら失敗したで、また最初からやり直そうと思う。」
'Even if I fail, I will do it again from the beginning.'
明日雨が降れば降ったでなんとかすればいい。
If it rains tomorrow, we can do something about it.
2That brings its own trouble
Once the wish comes true or things change, another side shows up, usually a new problem.
ニートになったらなったで大変だと思うよ。
Even if you become a NEET, I think it would still be tough.
大きい方が荷物とかいっぱい積めるけど、大きかったら大きいでデメリットがある。
The bigger one can carry lots of luggage and the like, but if it's big, there are also disadvantages.
Mixed up with
The same word is repeated to mean 'and then, with that very situation, something else follows'.
The form is the same whether the second part is relaxed ('we'll manage then') or resigned ('new problems'). Use the context to tell which.