Conversations Killers to Living Alone or with Roommates?

I have the tendency to jump into conversations that I am not suppose to be in because I feel that people are arguing when they say "There is no arguing going on".  Mostly this happens with my parents and myself but in the end, I make everything worse.  This is not something, I want to do but I am in the room, and can't listen to them almost arguing.

On the other side, I know that other members of my family also jump in when the conversation is not about them or they need to be in.  Sometimes when that happens, I can get upset and really angry because no one seems to understand that this is not their conversation.  I don't really know how to stop doing that but I know I am learning to keep to myself if the conversation is not about me.

As the quote above says, one word answers are what kills the conversation.  I never actually deeply thought that but that seems to be true.  I am the type of person who can't really start a conversation with people, jump in and have my say or go up to something and say something that will get us talking.  For the second one, jumping in, I actually have tried that often but by the time I am ready to jump in they are onto the next topic.  If there was a hand raising part, I would be the best at that but conversations at social events are popcorn style where anyone can talk at any point.

How do I actually talk to people in a way that will start a conversation and not just answer my question or have one word answers?

Along with that, I have been thinking about living on my own but I remember that most of what I do is on my own.  How would I be able to see, hear and talk to people everyday?  My job is mostly me sitting in a room on a computer which most days I don't see many people unless I have a volunteer-related event or meeting to go to.

Yet, I have lived with roommates before and that has been so-so.  If I really do live with them again, my criteria list needs to be longer.  Roommates are great at some points but a lot of times, I am not doing things on my own just tagging along with them as they pick what to do.

How do you choose between living alone or with roommates?