1

When I run:

bitcoin-cli getnewaddress

My bitcoin node returns me a brand new address. If I send BTC to this address, does the payment go to my main wallet.dat wallet (address generated from old/same private key). Or does bitcoind generate a new wallet/private key?

2

A wallet is not a single private key; it is an ever-growing collection of private keys. Each address has a private key stored in the wallet. Each time a new address is generated, so is a new private key. This is even true for HD wallets, albeit the private keys are generated and stored differently.

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