Thank you for all your suggestions...

I have not seen any of the things that Cathy mentioned, no respiratory,
cardiac, swallowing issues, no floppiness, no asymmetry.  He is an alert
little boy and bright-eyed after a feeding, he does have a 'small' face with
tiny features but I don't think this is abnormal.

I will readily admit, I'm still struggling with recognizing oral
abnormalities.  If this baby does have something it is minimal.  He does not
have a bubble palate.  He has an organized suck and the tongue protrudes
over the bottom gum.  I will look again to see if it lifts all the way to
the palate when crying.

But you have really directed me to something I haven't put a lot of thought
into, and that is the basis of all successful breastfeeding, the LATCH! 
(Doh!  Hitting forehead with heel of hand...)  I have been focusing on
supply issues, thinking that mom's supply was suboptimal due to short
infrequent feedings (in baby's first few weeks, due to other obligations),
or possibly age and stress.  She also has very small breasts, and therefore
smaller storage capacity.  So frequent feedings are important, but they
really shouldn't take an hour.

This baby probably does have latch issues, because mom does have very large
nipples, and as I've mentioned baby has tiny facial features.  Probably
means a small mouth too.  We've worked to get as much into his mouth as
possible, but his latch is not particularly asymmetric.  If he's not
efficiently removing milk, wouldn't this also explain why he's fussy at the
breast?  I've always thought he appeared frustrated, like he's hungry but
not getting anything.

Does this sound like a good plan?:

-Work on getting latch more asymmetric and absolutely as much areola as baby
can take.

-Nurse and compress only while baby is actively sucking, them pump
(immediately after feeding?  one hour after?)

-Spoon or cup feed EBM to supplement (we really hope to avoid formula since
dad has many food allergies)

-Discuss exclusion diet; I think mom is open to making changes

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