Certain problem domains require baseline familiarity with the subject. Far more people can recite the old "30 days has September, April, June, and November" rhyme than can explain what the words commutative and associative mean. Date math may annoy pure mathematicians but normal humans are used to working with calendars.
In the problem domain of dates, 'plus' is analogous to (but not exactly) its mathematical counterpart, and Joda's month math is almost always exactly what you want. Furthermore, plusIshRoundCeiling doesn't really explain anything; ceiling of what? The OP suggests that the cognitive dissonance is beneficial to the user. In which case it might as well be plusAsterisk or plusDontForgetToReadTheDocumentation.
The problem with plusGoReadTheDocs et al is that all problem domains have little edge cases like this. Excepting pure math, every single plus method is going to have notes. It'll be worse than those useless Prop 65 warnings in California.
Joda did this one right. Date math is simply not associative or commutative. Thankfully, most people are familiar with calendars and have some intuitive sense of this already. Littering the API with special hints doesn't help.