What is the Protocol for Hitting on a Homeless Chick?

For the past year and a half, my commute has brought me through Downtown Crossing. While walking through the corridor that leads to the Ashmont/Braintree platform, I have noticed the rarest of  rare sights: an attractive homeless chick. She sits Indian-style up against the wall facing the stairs that come down from the Orange Line. I have seen her there almost every day for 2 years, except for when she had a baby. But now that her sign reads "Young and Homeless" instead of "Pregnant and Homeless," the question is, what is the protocol for hitting on homeless chicks? Do you just sit down on the ground next to them and start a conversation? I have seen her talking to people before so I know she is capable of holding a conversation. I am guessing she is a runaway and just needs a helping hand/dick. Is it even worth it to hit on a homeless girl? If she is like most every other girl I have tried to fuck, she will reject me. Getting turned down by a girl who uses cardboard as a pillow would definitely put me in the express lane to Blowmybrainsoutville. This girl has some good qualities to her however so a pro/con list is in order for me to decide whether or not I should try and bag the bag lady.

Pro: Easily the hottest homeless chick I have ever seen.
Con: That still only makes her like a regular chick 5. 6 at most.

Pro: Seems to have a freckly face and red hair, quality traits in my book.
Con: Possibility she has not showered in 3 years and has a permanent "rusty" look to her.

Pro: Always has a different book by her side, so she knows how to read.
Con: Could have just stolen the books to use the pages as toilet paper.

Pro: Was once pregnant, so you  know she fucks.
Con: God only knows what happened to that baby.

This is uncharted territory. I don't know of anyone that has ever hit on a homeless chick. There is probably a good reason for that and the fact that this cute little dirty ginger could very well be a baby murderer is enough to keep me away. Also my girlfriend would kill me if I brought home a homeless chick.