No your worries and questions are not silly. They're very valid! And it's great that you're sitll trying to breastfeed your baby!!
I dont't have flat nipples so I can't really help you there. As for electric breast pump, you might want to try Avent ones. I have the Avent manual pump but I believe the electric one is easier. The Avent one is cheaper than Medela and Ameda.
It's only day 5. You definitely have milk. The milk supply works on supply and demand. The more you stimulate, the more milk your breasts will produce.
As for external help.. Possible to get mum or mother in law to come and help you out???