Hi,
Wow, I remember those early bf'ing days so well... it can be so hard! The first thing I would recommend is seeing if your friend can see a lactation consultant. I did with my first, and it was the best thing I ever did. She helped with the latch, which really is very important. It can be hard to help with this without seeing what's going on. While baby is still so young, his mother's milk will still be a lot of colostrum, with mature milk replacing that more and more. I don't think you can say that after a certain length of time the hind milk starts, it depends very much on how the baby is drinking etc. I know a lot of young babies do take an hour per feed, but if the latch is not good, then probably he is not feeding as efficiently/well as he could. A good latch will do wonders for the sore nipple problem! Ideally she should feed for as long as he wants it - trying to keep him awake of course! Check to see whether he's still actually drinking (swallowing). Some babies will pull off themselves when they're done. With dd1 I fed off both sides (once she'd had her fill on the first side I would change her nappy, then offer the second side, then the next feed time start off with the second breast). With dd2 at that age I was only feeding off one breast at a time.
Yes, I would wake every 3 hours (during the day) if her ds is still sleeping. I know that this can be really hard to do (sometimes it would take me an hour to wake my dd2!), but it really helps with building up milk supply, as well as helping baby to keep their longer sleeping times for at night. However he may wake 3hrly (or 2hrly even) round the clock at this stage. If he's awake earlier than 3hrs, then feed him! Don't make him wait!
At this stage it would be better not to be supplementing with formula, as her body is still working out the supply required.
What is she expressing for? Does she want to give bottles of ebm? With dd1 I expressed to relieve pressure off the 'unused' breast and to keep it stimulated (dd1 could not latch on for a couple of days on one side since I was so engorged). Warm compresses, massage, etc helped to express more milk. I expressed straight after the feed, but that was off the 'unused' breast.
I tried a dream feed at that age with dd2, but it didn't work... She would be so sound asleep, then waking her for the feed meant she wouldn't go back to sleep for hours! I tried that at a later age. Probably the nappy will need changing at each feed at this age, since they poop so often.
Hope that helps some, I'm sure others will give more advice! Tell your friend that it does get easier, especially with some help! Good on you for supporting her.