I think it is quite clear from the Prologue of this excellent tale that the Wife clearly sees no issues at all with being married so many times. On the contrary, one of the reasons that she is going on the pilgrimage is to get her sixth husband. She is certainly something of a coquette and a flirt, and is very proud of her marriage history:
For ever since I was twelve years of age,
Thanks be to God, I've had no less than five
Husbands at church door--if one may believe
I could be wed so often legally!
Not only does she take pride in her history and make jokes about it, she then interprets the Bible to support her position that marriage is good and we can remarry any amount of times we want to:
All my born days, I've never heard as yet
Of any given number or limit,
However folk surmise or interpret.
All I know for sure is, God has plainly
Bidden us to increase and multiply--
A noble text, and one I understand!
The way in which she focuses on parts of the Bible that support her position and conveniently ignores or argues against those that refute what she believes clearly displays the way in which she feels there is nothing wrong with remarriage. On the contrary, she uses her beauty and confidence to make advantageous marriages to increase her wealth and social status.