'If you will' is used as a way of making a concession in a sentence:
He wasn't a very honest person, a liar if you will.
Here, it is used a way of accepting that the reader or listener might think of the person as a liar, but without commit the writer or speaker to that position fully.
If you say something in all honesty, you are telling the complete truth. It can be used as a way of introducing a negative opinion whilst trying to be polite; in all honesty, I have to say that I wasn't very impressed.
This phrase may be used to mean 'approximately' or 'more or less'. I think it may have a sarcastic connotation in that the individual listening needed 'so many words' to get the point. It also may suggest the effort on the part of the speaker to explain an unpleasant truth or difficult concept.