My Bitch is having a rough go of it.  1st born still born with defect of insides outside of body. 2nd live 3rd still born 4th live 5th stillborn

2nd was born 12 min after 1st
3rd born 30 minutes after 2nd
4th born 10 minutes after 3rd and
5th born 30 minutes after 4th

What could possibly be going on?

If they're being born from alternative uterine horns it could suggest a problem with one of the horns. I had a bitch who ended up with a c-section, when they opened her up, the puppies were all in one horn, the other was full of pus. I'd keep a very close eye on your girl after whelping as you could have a similar scenario.

I'd agree, as it is claimed pups are born from alternating horns, then something went wrong with that horn, be it infection or trauma.

How long after would problems show themselves? 
It has been about 7 hours now since the last pup

Update #'s 6 and 7 born still born too. #8 lived #9 died.
#1 and 7 born with insides outside body

So sorry for your losses. I hope your girl is ok.  Have you given Bravecto as it can cause this - link to a previous post by Rabid

http://forum.champdogs.co.uk/topic_show.pl?tid=145487

So sorry to hear this.
Four years ago my girl had her second and last litter. She had six pups, same as her previous litter. No problems during pregnancy and easy labour. First was stillborn, second live and remaining all stillborn. All looked beautiful, perfect and good sized, just born sleeping. Never able to establish reason.
Thankfully mum was fine, she actually had it easy with a good pregnancy and easy time with just one pup to feed. Bless her she found five toys to replace her lost ones and kept them in whelping box for first couple of weeks.
Our miracle boy thrived (he was a fat slug) and we still see him often.

Puppies born with their insides out seems to be linked to some traumatic/disruptive event in mid pregnancy.  Birth defects most often occur in canines in the second trimester.

Contact with agricultural sprays, such as pesticides weed killers have all been implicated.

As for problems for the bitch, there is risk of uterine infection from decomposing pups, or whatever infection caused pups to die.

With that level of stillbirth and guts of pups exposed I'd want bitch on a course of Antibiotics.

I think 'insides out' can also be hereditary.   There was a line in my main breed that used to produce these all too often.

Insides out is gastroshisis or omphalocele (in omphalocele the intestines are outside the abdomen but  inside a transparent bubble of peritoneum, in gastroshisis they are not). Both are midline defects which occur when the foetus is forming and can be genetic or caused by a teratogen (toxin) or if some other trauma interrupts development at that stage. A (human obviously) cousin of mine had gastroshisis, in their case it was determined to be genetic.

I'd certainly not do a repeat or similar pairing again.