How does "The Raven" relate to Poe's real life, aside from paralleling his grief for his wife Virginia?

Perhaps it doesn't.

If you want to, you can definitely point out the various tragedies of Poe's real life, the struggles he endured that involved everything from gambling debts to drinking to strained familial relationships to the death of his wife, and you can find reflections of those struggles in his stories and poems about tortured souls, especially in his poem "The Raven." In fact, Richard Kopley suggests in his introduction to The Raven and...

Perhaps it doesn't.

If you want to, you can definitely point out the various tragedies of Poe's real life, the struggles he endured that involved everything from gambling debts to drinking to strained familial relationships to the death of his wife, and you can find reflections of those struggles in his stories and poems about tortured souls, especially in his poem "The Raven." In fact, Richard Kopley suggests in his introduction to The Raven and Other Poems that "an appreciation of the losses that Poe had endured in his life increases our understanding" of Poe's work.

But if you're trying to look too closely to confirm your guess that the poem and the poet's life have deeper parallels, you may not be successful.

However, we do have some hints about what Poe was thinking when he wrote "The Raven."

For example, we do know that he wanted us to interpret the bird as a symbol of memory. He wanted us to understand the raven itself as the embodiment of a terribly sad, ongoing remembrance. (I'm getting this from Kopley's introduction that I mentioned a moment ago.) This makes sense when you think of how the bird can only say the same phrase again and again: it reveals how we find only limited comfort in our memory of people we've lost, since we can only access recollections of the finite things they said and did, since they will no longer say or do anything else or continue to interact with us. 

We also have some extensive commentary from Poe himself on what he was trying to accomplish, literary-wise, by writing "The Raven." You can find his thoughts in his published essay entitled "The Philosophy of Composition." You'll find a bunch of insights there, including the fact that he purposefully wrote that poem to appeal to popular taste as well as to the taste of the critics. That fact alone might convince us that Poe was primarily working to create a masterful (and profitable) piece of literature rather than use it to subtly express his own personal struggles.