No, sending PDB files does not make obfuscation useless. Note, however, that PDB files may contain local variable names, so this is another piece of information that a disassembler such as Reflector can use. PDB files can also contain the full paths of source code files, however this rarely does any harm in terms of revealing confidential information.
Some obfuscators, such as Crypto Obfuscator, support the creation of PDB files - after obfuscation, it displays new PDB files that synchronize with obfuscated assemblies, your stack traces remain correct. In addition, PDB files contain obfuscated source file names mentioned above. It also removes all local variable names from PDB files.
DISCLAIMER: I work for LogicNP Software, a developer of Crypto Obfuscator.
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