I tried him in my girlfriends Ergo's yesterday and he hated it. I think because he really likes to face out - not toward me - so he felt confined. Maybe one of those back-pack standing things is the way to go. Anyone have any good recommendations for a style/type?
Since he's not used to sitting towards you, that just means he probably needs more time to get used to it. Do you carry him on your hip so his legs are more open than when he was forward-facing in the bjorn? If so, he's used to that a bit, and just might need a bit more practice. Sitting in the Ergo is totally different than the way they hang from the bjorn; there is much more support for the pelvis, so it'll take some getting used to.
Also, the key part of babies in babywearing devices is to put baby in and GET OUT of the house. YOu have to start moving immediately, generally, and not just inside. Getting outside and taking a walk will get almost every unhappy-seeming kiddo happy again. They are usually not unhappy with being worn, they are just unhappy that they aren't on the go.
Since you have an Ergo that maybe you can borrow I wont' suggest a mei tai, but this is me and DS when he was 16 months old at
Disneyland.
You would not believe the amount of "flirting" a kid can do with strangers when the strangers aren't being seen by the parents. Strangers do the silliest things when not scrutinized (either I have eyes in the back of my head or I know what I do, or maybe I have family tell me what strangers are doing, LOL), and it's great fun for the little ones. And when they've had enough, they put their heads on you and rest a bit. In that picture, DS is a bit lower than normal; I was having the hardest time shoring that thing up that day!
Of course at 1 he could easily go into a back carry.
Here's me and my guy when he was 2, with the Ergo.
Especially if you can practice with him now, he can get very happy being up with everyone, seeing what you see (or the crazy people behind you). It's much more comfortable for you to have him up there, rather than worrying about all the railings he's licking, what's on the ground that he's going to put his hands in, is he going to bolt under a railing into the other part of the line, and so on. Much better on your back, too.
Good luck!