Modeling props with Max
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Making models in 3ds Max for Source is the same process as making models for Half-Life 1.
Build your geometry, apply a bitmap material with the same name (or names, if a multi/sub-object) as the materials that will be applied to it, and export as an .smd file.
For example, if you want your model to have a material such as materials/mymats/misc_mat_01.vmt applied to it, then in Max you would apply a bitmap material called misc_mat_01 to it. The path of the bitmap is not important, as the material path is specified in the model's .QC file. Also, the format of the image used does not matter - just the name.