Having never bred a litter before, I often wonder if the first litter is a real learning curve and the other litters are easier? Or do you learn something new every time?

Both really.  I had my first litter over 15 years ago now, labour didn't seem to be progressing very well so frequent trips to the vet for Oxytocin.  With all the books, forums and internet now, it is easier to get information and advice to help.  I had a hermaphrodite in that litter which was PTS, very upsetting but thankfully never experienced that again.
Yes, you can often learn something new every time, no 2 deliveries/litters are the same, even from the same bitch - just be thankful that puppies arrive safe and sound and mum is happy.
The Book of the Bitch is a very good read and of course Champdogs for advice

All different, later litters teach you not to be complacent.

If first litter or two go well it is easy to think all these people saying how hard/heartbreaking/expensive etc breeding is are over egging the pudding.

Easy least you think, until the first time you have stillborn pups, pups that die, worse pups that are not right in some way that you still try to save and then have to accept they need to be put to sleep.

C sections, when is it needed? MASTITIS hand reading?

Worst of all realizing you made a poor choice of home for a pup, and having to deal with the consequences. Having them back to rehome is an inconvenience,  but better than trying to support them in a home that has turned out to be less than ideal over time.

An owner who inadvisably allows your precious pup to produce a cross bred litter when no-one will allow use of stud as they haven't facilities or ability to rear a litter, and then deal with having to try and home a litter at 12 weeks they can't sell!

Then there is the disappointment of your swans turning into geese despite what looked great on paper and how well the parents seemed to complement each other, and how promising the pups looked and acted at 6-8 weeks.

YOU REALISE THAT BREEDING WORTHWHILE DOGS HAS A HUGE COMPONENT OF LUCK!!!

Fantastic post, Brainless !

Their all different and wondering why the hell you wanted to sometimes.
But when your sitting watching them sleeping it's all worth it.

Always learning.   Each litter brought up something new to learn.   Just like however many time a person moves house - no two are the same

My first litter was really a disaster - crashed the car en route from Toronto to Philadelphia in the middle of Winter.   Two puppies only one DOA and the survivor a male and I couldn't keep another male.   At that point perhaps I should have called it quits but having seen what might be by the time another year passed, I went back to the same sire and that produced 5 puppies, one, bitch, I kept and a friend had the best dog.   Both gained their Ch. title out there and I was then away and running.   Hooked.   The worst part of all of it was the whelping, and then the parting with those I couldn't keep

If I learnt anything it was always to expect the unexpected.   And perhaps don't try breeding BASSETS     It was a real eye opener to come back to the UK and live for a year or two with people who bred Jackies.   Talk about 'wham bang thank you mam' with the breeding, and then come whelping, like shelling peas.

Trust your gut!
My first litter resulted in a 4am call to my girls breeder saying 'something doesn't feel right) when my bitch had failed to progress. To the vets it was and an emergency section and 2 pups wedged meant that she would never have got them out naturally.
It was a bit of a scary experience to be honest, sitting in the waiting room waiting for pups to be brought to me, wondering if I was about to be responsible for the death of my bitch. It did all end well, and I'm back a year later having another litter. I do feel nervous about the birth, but I think I learnt a lot the first time, despite it being horrendous at the time!

The whelping and raising the puppies for me have always been fine (Iv just been lucky) it's the people that Iv struggled with.

I helped my parents with litters when I was younger, I was  rosey cheeked and bushey tailed but after my first solo litter my perspective very quickly changed... I learned to never do business with 'friends' and not to trust people, basically if paper proof is not provided it's probably a lie, the kennel club don't stick to their own endorsements and problems are covered up left right and centre, which you later find out when it proverbially bites you in the arse. Having that litter I did get to meet some lovely people but my whole breeding out look changed very quickly.

I'm glad my bitches so far have had smaller litters, I am terrified of selling to the wrong people. A puppy from my first litter went to people seemed perfect, but as it turned out, they didn't tell me when there was a problem developing, and then ignored my advice to seek a specialist and the dog was pts at only 6 years old on the general vet's advice, without ever having been seen by a specialist, so we have no idea what was really wrong or whether that was the right decision. 2 of the puppies from my latest litter are owned by friends, and though at least I know I can trust them to take care of the puppies properly, it terrifies me in case something unexpected happens, as is always possible with living creatures, and they have a tragedy. It's a nightmare either way. Frankly I'd be happy if the litter I am currently planning could just have the perfect puppy I want to keep and perhaps a puppy for my friend who has the other dog from that first litter, and then I wouldn't have the stress of finding homes. :-)

My first litter last year I lost one. Had 3 boys 1 girl so kept the girl as don't keep boys. Then suffered domestic violence so have a female that is not socialised as was too scared to take dogs or kids out.So she is pet and not showable. On a good note from that litter he has qualified for Crufts