I've been following this thread, thinking that what I would do is nothing
special worth posting about, but I haven't seen it mentioned, either.
 Although many babies can latch almost unassisted, I teach all moms in my
classes how to make a "breast sandwich" just in case they have that baby who
needs extra help.  It utilizes the "C" and "U" holds, but is more than
supporting the breast. I show moms how to use the C (for football hold) or U
(for cradle and transition hold) with their fingers about 2" back from the
nipple tip to form a sandwich or wedge that baby can more easily get his
mouth around.  Mom's fingertips need to be on either side of the nipple so
that you can draw a straight line from the thumb tip, through the nipple to
the other finger tip. This is important, because most moms will have their
fingers above the nipple and the web of their hand smashed into the breast,
getting in baby's way.  When they have done this, the breast sandwich should
have formed a somewhat taut wedge of breast that makes a decent "landmark"
for baby to latch on to.  I find that it can be very important for mom to
maintain this hold during the feeding for the first week or so as baby
becomes accustomed to breastfeeding. If she lets go early, the first time the
baby loses suction slightly the breast will pull back and baby will either
slide down to the end of the nipple or lose the breast completely, having
lost his "landmark".  I also find that some gentle, assertive help in coming
to the breast aids him in "going for it".

Please forgive me if I've been reiterating the obvious.

-Lisa Marasco, BA, IBCLC