I can't help but wonder why Bear couldn't travel with you, unless you are going out of the country. There are a number of us here who travel with our birds, with great success! My Grey has a travel cage that is large enough that I don't feel bad having him spend a few days in, ensuring that he gets a lot of time out when I am indoors, or using the harness to give him some freedom when we are outside. I am also planning on adding the Celtei (spelling?) Pak-O-Bird for this summer season.
My parents live a good 8 hours away from me, Paco goes with me and loves it. I have yet to find a hotel that has refused me for having a grey with me, I just have to assure them that he will always be caged (I cross my fingers on that promise) and that I will not leave him in the room alone, not a problem, he goes with me.
If travelling with you is not an option, then make sure that whoever will be looking after Bear is known (and liked) by Bear and prepare yourself to face that that person may become his "favourite" over you. Greys are one person birds at the best of times, learning to tolerate others only. I also read on here not to leave my bird until I've had him for at least a year, or face breaking the bond that we have built. So, that being said, I've not done a weekend away, dinners/nights out mean that I take the morning off work to ensure that enough time is spent with the bird, the television is on a timer, the lights are on a timer, and I always make sure that I am the one to greet him in the morning.
As far as getting a second bird, I agree with Dave and Jayd, I would only get a second bird because I wanted to have a second bird. Earlier, I thought it was a great idea, but as I've noticed the changes in the last few months, I know I can't handle another. Besides, I'm only one person, I wouldn't be able to give two birds the fun experiences out and about as I am able to offer Paco. Also, Dave eludes to ulterior motives for a breeder telling you to get another bird, are they just looking to make a buck off another bird sale? Dave is very respected for his knowledge and experience, as Jayd said, he is both an owner and a breeder, use the advice they are giving you.
Private message Judygram and ask her to send you the link that she used to get her travel cage. She and I have the same cage, we are both happy with them, and she too travels with her bird. She always has the best links at the touch of her fingers.
Good luck with whatever you decide.
Ryan