Yes, this happens when the same key is used perform multiple signatures with the same R value - simply using the same key for multiple, sanely produced signatures with a different R value will not result in leakage, no matter how many such signatures you make.
Modern wallets use a deterministic nonce via RFC 6979.
ECDSA signing uses a random number called the nonce. A signature contains two numbers (r, S). r is generated only from the nonce and the nonce mustn't be reused. When the nonce is reused, r is the same too.
https://www.maximintegrated.com/en/design/technical-documents/tutorials/5/5767.html Eq 2 shows how r only depends on the S.
I don't know what you're ...
A private key is retrievable if two different messages are signed using the same r value and the same private key. Two signatures using different values for r are insufficient to recover a private key.
You are asking for help to break one of the core cryptographic assumptions that make Bitcoin work. If what you are trying to do were possible, ECDSA would be ...