Just to give my 2cents,

WW won't transfer the morphs from V3, or any other figures that it's using as a base character. However, if the clothing already has morphs and if you are converting that to fit V3 or any other supported character, then yes, there's a way you can transfer morphs.

I don't have tailor so I can't answer about that.

As for the difference between CC and WW, in CC, you have to make the adjustments manually. In WW, it converts the clothing to fit the character automatically. Just to give you an example, making adjustments to clothing in CC is like using the magnets and trans dials in Poser to make the cloth fit. You have to make those changes manually.

As a side note, WW can also convert clothes to fit morphed character. So if you want to fit your jacket to a morphed V3, then it is possible to do so. (I havn't done this but, if the clothing is converted to fit morphed V3, maybe the morphs can be exported and loaded as a morph target as a way of transfering morphs from characters to cloth?)