Can two consecutive の particles be used in the following way?

Question

We can use の as a substitute in successive sentences for something we've already mentioned so that we don't need to keep saying what it is:

• どのTシャツが好き？　→　赤いのが好き。

Then there is the possessive/associative の:

• 家の屋根、空の鳥、etc.

I was telling my friend about a new wallet I bought. By implication (or obviousness), it means the wallet I had before is now the "old wallet". So I wanted to talk about the contents of the old wallet. Can I use these two のs consecutively to describe them, like:

• 古いの　の　中身

Is this grammatical? Used? Or would it be better to just say 古い｛財布・もの・やつ｝の中身?

Answer 1

The first の is the pronoun の.
The second の is the genitive の.

There are two possible sequences of these two のs:

1. genitive + pronoun:　 この本は花子ののだ。 "This book is Hanako's."

2. pronoun + genitive:　 赤いのの表紙　"the cover of the red one"

In the former, the sequence of two のs is ungrammatical; you have to delete one of them.
In the latter, the sequence of two のs is okay.

(Examples adapted from a draft version of Hiraiwa's Constraining Doubling, although there are a number of publications on this subject--see the references section of the linked paper for further discussion.)