My two penneth for what it is worth.
In your first year go for the Bailey and catering. The Bailey is where it is at vis-a-vis Cuths life with access to the main bar). Unless you become a proctor or special-case you will have only one opportunity to live there. Make the most of it. Sharing a room (which becomes likely on the Bailey) is not as bad as you think it will be and the college food is convenient and, again, not that bad.
Bare in mind that there is no way of determining who your mates will be once you get here. Depending on the type of person you are and the things that you want to do, your friends could be from all around the place. If so, you accommodation in the first year is just a place where you sleep.
There is no way of guaranteeing you a place on the Bailey, but you might as well try to get a room there since you can live in Brooks House in other years if you so wish.