I always remind the moms I see that pumping is a learned art.  Whether they
choose to hand express, manual pump or they go for an electric pump, it takes
a little practice and sometimes some relaxation techniques to get a letdown.
 I used a hospital grade pump while my son was in the ICN.  When I brought
him home we were still learning about breastfeeding. I couldn't seem to get a
letdown without hearing the gentle shh-ha, shh-ha of the pump sitting next to
me.  So I rented the pump another week just for the auditory stimulation.  I
also seem to respond to foghorns.  Guess I'm just an auditory learner.

I have moms try double pumping first.  Sure, it's a little more awkward (okay
so I've got my nipples centered and I'm holding onto the kit, so how do I
flip the switch?)  and I've heard my share of cow jokes, but it is faster.
You could use the tricycle/bicycle analogy for this, too.

I tell moms they can layer their milk to store just the right amount in each
container.

I let moms know that some babies reverse-cycle nurse.  I accentuate the
positives here: your baby missed you during the day and this gives you some
one-on-one time,  breastfeeding can get you both back to sleep faster,
 they'll only be little for a short time...

I've had plenty of calls on Sunday nights from crying mothers who will be
back at work in less than twelve hours and their baby won't take a bottle.  A
few tricks I find effective are: 1.  practice when the baby isn't hungry( I
think the "when he gets hungry enough he'll take the bottle"  advice is
icky),
2.  have mom out of the house,
3.  don't try to get five ounces down him!  A modest goal of having the baby
accept the bottle at all is best.
4.  try with freshly expressed breastmilk
5.  use dripless, silicone nipples
6.. try having the baby sit upright on daddy's lap facing outward.  I've
found any position remotely resembling a Madonna hold can make a baby root
like crazy and fight the bottle.

I hope some of this helps.
Elizabeth Novelo Puzar, IBCLC