You can add as many skins as you want but beyond a certain number (I forget exactly how many - about 14 or 15) the skins will repeat and any beyond that amount will not show. I tested this by creating a large convoy of tramp steamers while I was working on the Merchant Variety Pack. Then again, this may have been due to some limitation with the single mission game mode...
I don't know about multiple skins for those two ships. I know the civilian version of the NAMC (NKGN) is multi-skin capable - I made a skin pack for it a long time ago, and it worked fine.
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