Past perfect sequence in reported speech

Context:

Yesterday, John was in the hospital visiting Bob, who was taken there the day before yesterday because he'd had an accident: the brakes on his car failed, his car rolled for some time, and he crashed into another car. While in the hospital John told me about the accident on the phone, and now I'm telling someone else about what John told me yesterday (I say one of the sentences below).

Sentences:

1. John told me yesterday that Bob was in bad shape after an accident, and that the brakes on his car had failed, his car had rolled for some time, and he had crashed into another car.

2. John told me yesterday that Bob had had an accident, and that the brakes on his car had failed, his car had rolled for some time, and he had crashed into another car.

Question

Is it correct to use three past perfects (as in sentence #1), and is it correct to use four past perfects (as in sentence #2)? Does that sound natural in the context given? Thanks.

Solution 1:

Both sentences are grammatically correct. However, they are quite long and 'wordy' for a natural conversation. In real life the dialogue would probably be something like:

A: John told me yesterday that Bob had had an accident.

B: Oh, no! Did John say what happened?

A: It seems the brakes on his car failed... (goes on telling story in past tense).