Being a plain volunteer would offer you more flexibility in hours, but less in duties. Staffing would allow you to choose your department, and therefore your duties (assuming the department head would take you), but be a bit less flexible in hours since staff are required to work a certain number of hours to fulfill their staff obligation.
Although discounted rooms are usually offered for staff, it isn't necessary for you to take advantage of that. If you'd prefer to stick with getting a hotel room with your cosplay group, that's certainly still an option.
As for working -with- your friend, it would depend upon where you were staffing and what the duties required of you. Some departments, such as registration, everyone pretty much works in close proximity to one another. Other departments, such as mine (panels), often require you to be on your own for a stretch while you're monitoring a door. (I actually try to pair my staffers up when I can, but this isn't always possible.)
I don't think there is any task we can set you, whether staff or volunteer, and guarantee that the two of you can stay together constantly, unless one of you were staff and the other were not... in which case the non-staffer might in some cases be free to hang about so long as they didn't distract you from your duties.
I can't say whether your health issues would be an issue without knowing what they are, so I won't comment on that. That'd probably be something you should discuss with the dept. head of whatever department you decide to apply to. ^^
-Kava
Thank you very much. My health problems are my dysfunctional digestive system, knee problems and depression, so I can't run/stand long periods, need to sleep a lot from medications, and have to closely monitor what I eat along with stress... the stress being a big issue. I wouldn't except to work with someone 24/7 but I would prefer to as it helps lower stress, therefore would make me more productive. I wish there was a way to help only certain days, but I guess that would undermine the position as being "staff". I'll probably just wait another year before trying to work.
However, I know one thing I could do is setup and breakdown of tables and such like in the dealer's room, though I wouldn't know who to even ask about that. It's not much, but I'd feel better knowing I was helping, even if only a little.