Mom bf'd seven of us and the hardest was my youngest sister, 2 months early - she says "each baby is different," in terms of nursing. But she was able to establish a good supply for my sister in the early 80's despite her being so premature.
My older sister didn't have any trouble getting going on bf with her three, nor did my aunts with their (5 and 3) nor my cousin. I didn't have trouble at first, but hit a major bump at about 2 months when Ina started limiting feeds for reflux pain, I was told to supplement per Ped/LC both (but both assumed I knew to pump to maintain/increase supply because I was so informed -- but I was too sleep deprived to think of that at that point) - and we discovered I'd some retained placental fragments which were impacting my supply too. So, I did struggle quite a bit for awhile. I guess I knew it could be easy when we got back on track though ....
I think moms need to know that it's not *always* awful, but it's not *always* sunshine and roses, either -- but it's worth the work regardless, and that once established, bf can be way convenient and a wonderful part of parenting. The big thing is for all moms to know to:
A. Do your research, buy/read breastfeeding books!
B. Find bf-knowledgeable and supportive OB's and Peds.
C. Research local LLL and LC support availability.
D. (Most important of all) Ask for help!!! Don't assume that you'll be judged, or that you're overreacting!!!
E. Double-check the advice you're given (in re: meds, treatment approaches, bf routines, etc.).
I do think, whether we assume bf will be easy (I did, although I did a lot of research anyway so I knew it might not be) -- or whether we assume it'll be difficult, we DO assume that it's "natural." And the reality is that for many women, it's something they've seldom seen and have little experience with, and they often are surrounded by people with even less knowledge/experience than the mom, who are supposed to be supporting her.
I think it's great to share "it was easy for me" stories - and I think a lot of us temper our "Well, things were rough" stories so as not to scare people (my approach is usually to say "Inform yourself, read these books, don't hesitate to call an LC, mine was wonderful!") .... I think that deviating from the norm is always a bit scary for most people -- and the norm is either ff, or bf only briefly in our society. So whether women hear horror stories or "it's all good" stories, they may worry either way about their reality vs. what they've been told.
That said - I also think that positive thinking can make a huge difference, too. I think that a lot of the uncertainty and fear which some women feel going into childbirth, helps promote the pain (and "I need meds" reaction) which they feel during labor ... and I think that moms who are terrified of supply issues, latch issues, etc. - probably end up with a bit of a self-fulfilling prophesy going on too sometimes.
(I also agree that the medications and interventions at the hospital can really negatively impact breastfeeding initiation for mothers, and can have effects which mom is still fighting a month later