We've been using nipple shields from week 2 up until a few days ago when LO surprised me by consenting to latch without *happy dance*
We wouldn't still be breastfeeding if it wasn't for the nipple shields, and I'd happily use them in public (though I tended to try and find corners so I could be discreet when putting them on.) Don't get me wrong, they were a complete faff, but in comparison to having to pump in advance or carry a breast pump around with me if I was going out for the day, they were a godsend.
We also used to nurse lying down at night like a PP by the light of the Angelcare monitor, though I still used (and still do) wake up because for some reason I get quite bad nursing agitation when I nurse lying down, and the only way to get through it is to distract myself by reading a book.
As for pumping, I don't think you'll need to if LO is nursing at the boob until they fall off of their own accord. As long as nappies are wet, etc, etc...