I wrapped DP into the HAB we had with DS a few times then he learnt to do it himself. He didn't really like using the shoulder sling. He used the Ergo far more confidently when it was time to move onto the Ergo and could get him on the front way and the back way no problem in no time!
I've got a new wrap sling coming in the post (it's a close weave cotton) and he said he'd wear it - it was custom made and I showed him the fabric before it was cut and he stil said he'd wear it; it has green, brown and dusty pink horizontal stripes on a white background and it didn't bother him at all But he'll get more of a wearing chance when the next kidlet is a bit older and by then we may be using the Ergo.