As someone that does research into Bitcoin privacy I can tell you that strong privacy guarantees are extremely hard to achieve in Bitcoin.
1. Your IP address can often be associated with the Bitcoin transactions you create.
2. TOR can make this harder, but fingerprinting a particular Bitcoin wallet between TOR and clearnet is very possible.
3. Almost all tumblers in current use must be trusted not to violate your privacy, that is they know who is who and must be trusted to not tell third parties. I would suspect that some tumblers are run by LEOs. Even if a tumbler is keeping your secrets they may not offer that much protection against blockchain analysis. It is hard to tell that a tumbler is actually providing any on-blockchain privacy.
Bitcoin and cryptocurrency privacy is likely to dramatically improve over the next five years, but right now there isn't much actually deployed.
1. Your IP address can often be associated with the Bitcoin transactions you create.
2. TOR can make this harder, but fingerprinting a particular Bitcoin wallet between TOR and clearnet is very possible.
3. Almost all tumblers in current use must be trusted not to violate your privacy, that is they know who is who and must be trusted to not tell third parties. I would suspect that some tumblers are run by LEOs. Even if a tumbler is keeping your secrets they may not offer that much protection against blockchain analysis. It is hard to tell that a tumbler is actually providing any on-blockchain privacy.
Bitcoin and cryptocurrency privacy is likely to dramatically improve over the next five years, but right now there isn't much actually deployed.