Baby Wearing Help

I used a Maya wrap for all my babies and it worked amazingly and I was able to tighten or loosen it in any area I needed to obtain a comfortable desired snugness. The fabric is very breathable and strong. I used it from the day I started walking around with them to their toddler years.
I think it's wise to test out different baby carriers to see what works best for you and baby, ask around to see if you know anyone who would let you test drive their Maya wrap or any other sling/wrap/carrier.

Did you know there are baby wearing groups all over the country? I found one in my town. I went with my baby to one of their meetings and they were great. They had a bunch of carriers to try out, and they taught me how to do the moby properly.

If your location is correct, Tampa isn't too far and they appear to have a big active group: https://m.facebook.com/TampaBayBabywearing/. If you are not near Tampa, google babywearing and your location.

It was like Le Leche League for baby wearing :). My group even had a lending library so I could borrow different types of wraps for a month to try them out before buying. Look for a group in your area.

ETA: It is a lot easier to troubleshoot in person, but over the internet, my best advice is this - are you doing the hug hold or the kangaroo? If you are doing the hug hold, maybe try the kangaroo (google to know what I mean). When you do the moby in the kangaroo hold, the material in the front middle should be under the baby's bum only, not his feet. That's what supports his weight. You tuck the feet under the side wraps gently to keep him from wobbling, but his weight should not be on his feet. The stretchiness of the fabric shouldn't matter - I made my own moby-type wraps out of material that had very little stretch at all.

For the head support: as comfortable as I was wearing my baby, and I did it all the time, I always kind-of kept one hand on them. I would take it off for a minute or two when I needed both hands. But it was some kind of basic instinct to have a physical hand on the baby even though all the weight was supported by the wrap. So when tiny, my hand helped steady any head wobble. And once he was bigger, he had enough neck strength that I didn't worry about it. Also, for safety reasons, your baby's head should NEVER be at an angle or fully covered by the wrap. Your baby's head should be in the center of your chest above your breasts. If he's in the right place, you should be able to kiss the top of his head by simply bending your neck.

ETAA: I also used and loved ring slings and my Snugli carrier. Find a group and try them all!

As a breastfeeding and (semi) co sleeping mama I was never comfortable with a wrap or sling. I just never felt like my babies were comfy or safe, so I used an old school snugli/baby bjorn type carrier, and when they were older, a baby backpack type thing, from Land's End I think.
Go with your gut. Try a few different carriers until you find the one that works for YOU.

Loved my Baby Bjorn! And it was great as he grew. Do they still even make those??

My daughter uses the Moby wrap. She arranges it so baby is lying more sidewise.That way the head is supported and at that age baby curls his legs over his torso in the position he was in in the womb.

We were so exhausted from a colicky baby that we couldn't figure out the baby wrap.

Dr. Sears used to sell a babywearing product which was like a cross between a wrap and a Bjorn. I don't know if he still does, but you could check out his website: http://www.askdrsears.com

I never could get the hang of the wraps and I tried several. I had the best luck with the Ergo and used that until my son was two years old. I would recommend seeking out a specialty store or a support group. I didn't have discolored feet with my son so not sure about that issue. Good luck.

I hope you figure it out...I never did. My son hated being wrapped...turns out sensory issues.

My daughter loved it but her feet/legs turned an awful blue/purple color that worried me and so I stopped carrying her in a wrap.

I will be checking back to see what others tell you...I was at a loss and couldn't find help.
Good luck!!