One of my favourites is "Harry in the Hole" by James Gordon, a Canadian singer/songwriter; it's on the CDs "Mining for Gold" and "1 in 5" (the latter being an album devoted to mental health songs). The song is more about PTSD than homelessness, but the character is homeless and the song discusses the town's discomfort with him and his involuntary hospitalization. I especially like the lines: "When his capture finally came, it was not soldiers but his neighbours who took him from the safety he had found....It seems that Harry's enemies were real, they were you and me, though he had eluded us for years..."

Harry in the Hole (James Gordon)

They call him Harry in the hole
You'd see him walk out in the cold
With a sack upon his back in the wintertime
He looks scary, he looks old
For Harry in the hole
That really was his only crime.

You can't talk to Harry in the hole
He just stares and shrugs his shoulders
And shuffles silently along his way
Sometimes with terror in his eyes
You see him scan the northern skies
For an enemy that's stalked him all his days.

Round here stories are still told
How old Harry in the hole
Was a fighter pilot back in the war
They say his plane went down in flames
Harry never was the same
After he returned in 1944.

They say that Harry had survived
Deep behind the German line
By hiding in a hole beneath the wreckage of his plane
Now he lives out at the edge of town
In a hole he dug into the ground
Waiting for a foe he knows will someday come again.

He did not fit into their mould
Folks thought Harry in the hole
Was a stain upon the good name of this town
When his capture finally came
It was not soldiers but his neighbours
Who took him from the safety he had found.

It seems that Harry's enemies
Were real, they were you and me
Though he had eluded us for years
Now he's in the hospital
A hell that's more acceptable
A prisoner of all of our fears.

They call him Harry in the hole
You'd see him walk out in the cold
With a sack upon his back in the wintertime
He looks scary, he looks old
For Harry in the hole
That really was his only crime.