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Why do I need to measure bearing play when disassembling the trailing arms ?
That's a part of the "factory" bearing check/replacement strategy.
You check the endplay beore you take them apart so you have a "baseline" when you re-assemble. By knowing the initial endplay, and the thickness of the shim (when you take it apart) you can figure out what thickness shim you will need to give you the correct endplay on re-assembly.
Nobody I know follows the factory procedure.... we all use a "set up tool" of one sort or another.