When I buy a used book, as I do several times each year, I dislike finding the name of the previous owner inside the front cover. Somehow a book seems less mine when it bears someone else's name. I do understand why people put their names in their books. It may improve the chances, however slightly, of loaned books being returned someday. Yet books are like money. You can't take them with you. Whether you dispose of them or your heirs do, sooner or later they are likely to belong to somebody else. And that somebody probably will resent your name on their book.
Finding the name of some prominent person in a book changes things, of course, and it wouldn't have to be William Shakespeare. To own a book once owned by, say, C.S. Lewis or Audrey Hepburn or Harry Truman would be a thrill. You can't very well expect only famous people to put their names on their books, but when ordinary folks do it, it decreases rather than increases the value of those books.
I don't know that I have ever seen a book with more than two previous owners listed inside the cover. There are reasons for this other than the fact that relatively few people still write their names in their books. Few books ever have more than two, three or maybe four owners. Either the books fall apart by then or they show their age so much that nobody wants them on their shelves. People who still read old books usually prefer new editions of those old books. They don't want to read a 100-year-old copy of Moby-Dick. They'd prefer a slick new paperback.
A few quality editions of quality books are passed down from owner to owner for several generations, but they might be less likely to be passed down if they have a list of the names of those owners inside.