Do not reuse addresses
I haven't been adhering to this advice. I find it stressful/risky to generate new bitcoin addresses when sending large amounts of btc; sending to an existing address is much less nerve-wracking. Anybody have any methods for mitigating this stress?
A Bitcoin address contains a checksum, so even if you change just a single character the address will be detected as invalid and sending to it not possible.
Your wallet will also generate a new address every time you make a transfer from it with a change. So there is not really a reason not to use a new address every time.
A Bitcoin address contains a checksum, so even if you change just a single character the address will be detected as invalid and sending to it not possible.
Yes, Bitcoin is not Ethereum, where they don't have checksums for addresses. Which bank account numbers have since 1960s (Luhn algorithm).
Note that checksums are optional in bitcoin too, as sending directly to a pubkey is still a standard way to send money, at least at the protocol level; but it's not commonly supported by wallets, except in the case of taproot, where the common way to do that is to wrap it in a checksummed format anyway.
I'm not aware of any wallet that supports it except electrum, I think (I've never tested it). Taproot also uses a form of p2pk, though I'm not aware of any taproot-supporting wallet that lets you send to a "raw" pubkey; they all want it wrapped in the bc1p format, where there is a checksum.
Address reuse for large amounts are especially bad and potentially dangerous from perspective of your own safety. As other party basically sees all your transaction history and current balance.
Use a trusted open source tool (like Sparrow) for coordinating transactions. Verify the software (easy to do in Sparrow, under Tools > Verify Download). Run on an old laptop that's running nothing else but Sparrow.
Double check your address, before sending to it.
I can't think of anything else. Reusing your address is probably putting you at more risk, in terms of privacy.
Like with a lot of things, privacy isn't a binary thing, it's a scale. Address reuse doesn't immediately nullify your privacy, it merely reduces it. You have to decide whether the reduction in privacy is worth the confidence you gain by sending to a known-good address.
doubletriple check the address before sending. To be honest i wish wallets apps made this UX better.