I had the shitest possible start to breastfeeding and honestly it is a miracle I am still breastfeeding my DD. It honestly is the hardest thing I have ever done and also the thing I am most proud of achieving! (And now I know what to answer in a job interview if they ever ask that question!).
I scribbled some of the barriers to breastfeeding on a thread before when DD was 3 weeks old- but then MORE came up (lucky me! 
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So sorry I just have to post the list again plus the additions because I would quite like a little pat on the back from all you lovely mnetters, just to help me make it to 1 year (or more maybe)!
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Breast reduction 9 years ago (large reduction 7lbs taken out- one nipple doesnt function so well)- not even sure if I can breastfeed until I tried. HCP's all know this and assume am going to fail at breastfeeding so negative from outset.
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Flat nipples so baby can't latch on without the discovery of fabulous nipple shields (genetic issue but not helped by reduction), then had to wean her off them gradually so incase they affected supply. By 6 weeks she was feeding without them.
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Extremely raumatic delivery and baby in NICU for first 5 days- no cuddles for first 24 hours of baby's life, limited skin to skin- tricky with all tubes etc. Baby was oxygen starved (possible damage) and initially showed poor suck reflex but that improved within a day or so.
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Baby being tube fed my EBM every hour means baby full and has no interest in latching- keeps falling asleep at the boob- i have to maintain these nasogastric top ups but once they are reduced to three hourly I can sometimes also get her latched for a feed. Except I also still have to pump and invariably she gets hungry just after I have expressed and there is no more milk! Breastfeeding support at hospital limited (lactation consultant promised everyday and never materialised) had help from speech and language therapist with latch though which was fantastic.
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Baby has to have MRI, she is sedated with suppositories she keeps pooing out (effectively enemas)- she ends up going without a feed for 6 hours (at 8days old and already lost 10% of weight) due to the sedation, I pump in meantime but this mucks up the baby hungry, mums boobs full thing again plus difficult to get her feeding due to sedation. Loses yet more weight due to the "enemas".
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by day 7 breastfeeding was still a massive struggle as we had to always give her nasogastric tube 32ml top up every three hours and it was always at a time which caused her to fall asleep and not be awake for a feed. We hated that nasal tube and so did she - used to pull on it during breast feeds and would look uncomfy during top ups. So in the end we had to say no more tube feeds and do her top ups with a syringe in mouth (easyish) or cup (good skill to learn but spilt everywhere and resulted in very windy baby). This was kind of against medical advice as they wanted to keep tube feeds going but we persevered and as a result breastfeeding was able robe established must better basically because we stopped trying to work to nasal tube feed times and did three hourly breastfeeds plus top ups instead. The doctors were all freaking out and saying she is a big baby and you won't sustain he'd etc but it's what we had to do. With hindsight I think if more breastfeeding support had been available at hospital we would have figured out how to sync up the tube and breastfeeds but we aren't medical people so were just following instructions until they really stopped working for us but is scary to go against medical advice!
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First week after leaving hospital (12days old) Baby loses 14% of bodyweight in total (not helped my mri enemas etc). Sent to hospital for dehydration check- supoosed to take an hour- takes 7 (and results come back fine). I don?t have enough to eat or drink and feeding is tricky in hospital as doesn't have pillow etc, and its not home. Anyhow of her 14%weight loss the majority of that was in hospital and after her enema. She did still lose a tiny bit more once we went against medical advice with not tube feeding her, but it wasn't massive and her weight is now fine so it was the right but scary decision for us. Really had to battle with hospital not to readmit us (I would have lost my mind- being completely loopy from the 8days in hospital the week before)
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Baby put on intense regime of feeds- Every 3 hours -feed at breast, give 40ml top up, then pump next feeds top up then sterilise everything for next feed. We don't stop with the top ups really for about 10weeks.
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Baby is really slow to gain weight (6weeks to regain birthweight). Have to give a formula top up sometimes as don't have enough EBM.
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For first week of her life she had a canula in her arm for her antibiotics. This made feeding on the right breast very difficult as this sore arm would get in way and hurt her if positioned wrong and she didn't seem to feed as well in the rugby ball hold. creates supply issues in right breast.
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(just so I can make it 10 hurdles!!) Tongue tie discovered and snipped at 7 weeks- before this feeds could take up to two hours and were pretty relentless. Had bad cracked nipples that made me want to throw DD across the room with the pain and unfortunately post tongue tie snip meant dd had to relearn her latch and completely knacker my nipples again. Then also got infection in nip so it wouldn't heal. I had painful feeding from 10days to 16 weeks as a result (varying from agony and tears to grit teeth and curl toes. if it was agony all the time I would have definitely given up- as it was I just wore my teeth down from all the gritting!
For me breastfeeding wasn't easy or painfree until DD was 16weeks old and although it took weeks to wean dd off the formula top ups she is now predominantly bfed (bottle formula at bedtime as supply never got up to full capacity) so am a little bit proud of how far we have come (and almost never want to wean her because having finally got her going on the boob I don't want her to ever stop!- Although I probably draw the line at bfeeding a 12 year old!)