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My question is - does the timing of when a compromise offer is made dictate whether it is admissible or not?

Here's an example: A rear ends B in his car. A gets out, rushes up to B's car and says "I'm so sorry, I will pay you $2,000 for your damages."

I took Barbri for New York in February and distinctly remember Barbri saying that timing DOES matter and that a settlement offer made before there is a live dispute (such as in the example above) is admissible. I am taking Themis for VA in July and they just told me that the timing does not matter and all settlement offers regardless of when made are excluded.

Any thoughts on this?

And by a "live dispute", doesn't have to be a legal suit, just a controversy between two parties. According to Barbri, because B made the offer before A even exited his vehicle, looked at the damage and blamed B, there is no live dispute and as such, the offer is admissible.

I don't think timing is determinative but can be helpful.

In your example, A could be admitting liability but his $2000 offer could be interpreted as a dispute as to how much the damage is. If so, then at the very least, the portion re damage would not come in.

A statement that comes long after the crash is far more likely to be a compromise or settlement statement because at that point there really wouldn't be much other reason for the parties to be communicating.