Alright, I've frequented this specific forum for a bit now as I've tried to gather so much advice on how to approach a two year old Time Warner collection of $241 which was unfortunately made possible during my time as a college student. After biting the bullet and not having so much fear anymore, I chatted with Time Warner reps to see if I could get it paid off through them since they are the original owner of the debt. They told me they couldn't, and said to go through the collection agency.
Being a bit nervous, I called the collection agency and the representative was actually really nice. She informed me that the following information I give would be used to collect a debt, so I agreed - nothing about "We're not going to delete this off of your credit report." No negotiations, lowballing, anger, nothing. The rep was incredibly respectful.
Before I paid, I asked whether the collection would report as a zero balance on my Experian report or whether it would be deleted off of there entirely. She said both, and that the collection would be gone "during the next billing cycle next month, which is November."
It seems that I'm well on my way to getting this collection off of my account and finally will have a shot to gain back some points with Experian to get it on-par with Equifax and TransUnion scores. The only thing I'm curious about is that, what could "next billing cycle during November" mean? Am I suppose to just reload my account and see that it has been taken off? Also, would having Credit Sesame and ProtectMyID (both of which link up to Experian) be enough to track when this thing goes away? I am paying for three months of FICO 3-Bureau Credit Monitoring here on MyFICO, but I don't know whether that would actually tell me when this thing goes away.
Oh, and if I can give advice to anyone afraid to pay a small collection (granted mine isn't gone yet, but I hope the lady stays true to her word) - know that you'll be okay! It took me SEVEN months to confront my fears, which is way too long but I hope that I can influence someone and tell them that it's okay to deal with these things now. I hope to post another thread saying that "WOOHOO! MY COLLECTION IS DELETED!" like I've seen so much here. 
