I've never tried a wrap and originally rejected the idea as it all looked a bit complicated. We started with a close caboo, tried a Tula and Ergo (hated the waistband on both), and now have a Connecta and a Didytai Mei Dai, both of which DH and I love and use daily for walks, daytime naps etc (so far we've only done front carries). A friend is lending me a ring sling for the summer.
Would it be worth learning to wrap in terms of longer term comfort and flexibility (beyond the attraction of the gorgeous fabrics which I admit might be swaying me)? Or do the Connecta/Mei Tei cover everything we need? The Didytai is so soft and has given me confidence with lengths of fabric, which is why I'm now considering a wrap for the first time. DS is 5.5 months, I'm quite petite, I can't imagine carrying a 4 year old but I'd like to carry for a while yet if DS still enjoys it as it suits our lifestyle.
Unfortunately we are overseas and not near a sling library - but I could pay for a session with a babywearing consultant.