For all those things...
Well, you just kinda do 'em. Real life doesn't have a step-by-step tutorial. Just think of it all like ordering a pizza. A really big pizza that you a few people to help eat it. ^^
Go to the con's website and find out their official hotel, call the hotel and ask to reserve a room. I believe they will require a credit card on file to reserve one.
Finding roommates, either take some people you already know, since it's a con maybe you can room with some of your online friend? If you know them, consider them a possible roommate until they say no. You can also always use the con's forums, there's usually a few people last minute begging to be let into a room.
So you know, you're 18, right? Well, consider the age of who you want to bring with you. At a recent con, I tried to take the room I'd reserved and was turned away because I had my sister and one other friend who were 16 and 17, minors. It's legal for me to get a room with a bunch of 18 year olds, but you need to be 21 to have anyone under 18 in your room with you.
Shyness. No. At a con, it's very odd. You already have a common connection with people just for being there, so it's a LOT easier to talk to someone at a con than in real life. I mean, they're at a con, you obviously share an interest, eh? I recently met some awesome furs at an anime con and I'm going to be going with them when they go to AC this year, as well as they're going to be my con group for the next con I'm going to too.
It's hard to explain, but it's like, say if you identified a possible furry in public. Yesterday, I saw a girl wearing a little heart dog tag. Without even thinking about it, I approached this stranger and told her I liked her tag. She said she got it from Petco, I said that's where I'd got mine from too, but I don't wear it that often anymore, said bye since my group was leaving that store and parted ways.
Things like that make it easy to shatter the ice and the moment you start talking to someone, it's a lot easier to keep up the conversation.
"I love your suit! Is that an original character?"
"I like your ears! Did you buy them or make them yourself?"
"Ooh! Can I see your sketchbook?"