I recently read 
The Sense of Style: the Thinking Person's Guide to Writing in the 21st Century! by Steven Pinker.  Pinker covers everything that confuses and confounds writers.  :) 
For example, we all know a pronoun is a word that take the place of a noun.  In fact, there are different kinds of pronouns:
- A nominative generally is the subject, or actor, of the verb. Nominative pronouns are I, he, she, we, they, and who.
- An accusative generally is the object, or receiver, of the verb.  Accusative 
pronouns are me, him, her, us, them, and whom.
- Genitive is primarily a way to indicate possession; it's a noun that modifies another noun.  Genitive case is marked on pronouns: my, your, his, her, our, their, whose, its and on noun phrases with 's.
  I sometimes have trouble with I verusus me.  Using this information, a writer should write: I was down by the schoolyard. Or, even: Julio and I were down by the schoolyard.  
But a writer 
can write: Me and Julio were down by the schoolyard.
One of Pinker's messages is language evolves and writers should use their knowledge and experience to write what works for a particular piece.
Another tricky one for me is who versus whom.  But the nominative/accusative difference should pin it down.  Who kissed the bride?  Whom did Henry kiss?
What grammar issues do you find tricky?
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