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I think the best advice I've seen is to go into a store and try different ones out, if you have the chance. Personally, we have a Moby, Baby Bjorn, and Ergo Sport, and I haven't had any issues putting them on/taking them off by myself. However, I think some carriers fit some body types better, and if you can try a few different ones on, you'll be better able to figure out what works best for you.
In general, though, I do think the more you practice the easier it gets! :)
what i've found is that the more options they have/the more they grow with baby, the more complicated the are, lol. i have an ergo and OMG is it a PITA to use, but it's totally worth it because i've been using it since he was 4 weeks old, and now he's 16 months and it's still great for him. i also have a ring sling (maya wrap), a moby, and a seven sling. well, i don't have the moby any more...i regifted it to someone (who knew it was used) because i honestly didn't like it. the seven sling is great to just keep in my purse because it takes up so little space, but i've really only been using that and the ring sling since DS has been old enough for hip-hold, and i only use them for short carrying trips.
I think it's just preferance. My sister swears by her bjorn. Have you heard of the Mei Tai? I've carried 3 months to 3 year old in the Mei Tai with no issue.
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A coworker of my husbands let us try her baby bjorn to see if we liked it. I was surprised at how hard it was to put the baby in it. Are they all like that? Does it get easier if I use it often and get more used to it?
Thanks!