I am less concerned about any reasoning or timing issues and much more focused on the items themselves. (Of course, if one was to consider bidding, knowing such things would be important.) What an impressive collection! That this many items are up for auction which have been in the hands of the same person since Elvis gifted them to her 28 years ago is pretty awesome.
If I were in the market for an EP-owned item, I would definitely try for one of these items. The motorcycle jacket and then the ring would be my top choices.
I remember fairly recently that tour jacket and maybe some other things of Ginger's were listed on eBay. Some people wondered why she went that route; I guess she figured out that a reputable auction house was a better option.
Someone indicated to me that she never intends to sell her 11.5 carat engagement ring. Time will tell, I suppose.