Is "Southy" (or Southey?) a slur or term of endearment?

Depends on who's saying it.

Its just a way to say South Boston

No.

I am pretty sure its actually Southie.

Southie is a part of Boston...South Boston. Its neither a slur nor a term of endearment.

I'm from South Boston. I would say that "Southie" is a bit of a term of endearment, certainly not a slur.

I was born down on A street

Dragged up to B street

South Boston is my home town

If you want a punch in the belly

See T-Bone Kelly

He'll never let you down

We'll make you or brake

But never forsake you

South Boston is my hometown

...best sung by a large group of drunks.

They don't sing the words "South Boston is my home town." It's sung, "Southie is my home town."

I thought you said you were from Southie!

I grew up and live in Southie. I come home when I'm not in school. The term is used by locals to describe its neighborhoods as something short (southie, westie, eastie,) The neighborhood has changed significantly many of the people who lived and grew up there packed up and bought homes in the south shore. Many young professionals and young families have moved in and condos has been put in place. The media (the departed, good will hunting) depicts Irish Americans who are from Boston as corrupt and Mafia run. That is not the case 95% of the people I know from the neighborhood are good hard working people. Like every city or town people have short term names for certain places in their area.

Southie is actually a pretty damn nice place to live now. I couldnt afford to live there.

I've been watching a lot of Boston-based movies and TV shows lately, and I keep hearing characters use the phrase "wicked" to mean "very." I see that there is a definition for this word that relates it to Boston, but I'm not sure if it's actually used by Bostonians or if it's just a Hollywood thing. I need resumes planet to write my resume on time so that I could get good grades.

No. Any comments directed toward the South is never unwelcomed. They get what they get.