Since Boaz is taken by many (if not most) to be a figure of Christ and Ruth as a figure of the Church and since the man with one shoe is taken to be a figure of (some say) the first covenant or the legal rule as such, it does matter if there is thought to be ambiguity in regard to the issue of the shoe.
Therefore the kinsman said unto Boaz, Buy it for thee. So he drew off his shoe. Ruth 4:8 KJV
The referent (or antecedent) is 'kinsman'. The kinsman said ...
Although Boaz is mentioned next (said unto Boaz) it does not mean that the referent (antecedent) immediately changes to 'Boaz'. Grammatically, the referent/antecedent is still 'kinsman'.
It is he who takes off the shoe.
The question is, whose shoe did the kinsman loose ? His own or Boaz' ?
This is made clear by Deuteronomy :
Then shall his brother's wife come unto him in the presence of the elders, and loose his shoe from off his foot, and spit in his face, and shall answer and say, So shall it be done unto that man that will not build up his brother's house. Deuteronomy 25:9 :
Here the refused woman takes off the shoe of the kinsman who will not redeem and she spits in his face for not doing his brotherly duty towards her own (now deceased) husband.
But the kinsman of Boaz (nearer in relationship to Ruth and thus having precedence) admits of his own refusal and takes off his own shoe.
(Whether he spits in his own face is not recorded by the scripture.)
There is, of course, the issue of Ruth being not born of Israel but being a Moabitess. Therefore what rights does she have ?
Boaz does all that is needed for the Gentile woman and the man with one shoe does absolutely nothing. He has taken off his shoe and will make no further progress.