Congrats on the meeting with nct bf lady today, it sounds like it went really well. I too had to sort the head tilt out with my girl ( & a little more!)!
Good luck with silverets too, it's the first time I've heard of them on here, why didn't I log on months ago?!?!?
As for expressing, I was told officially not to start til 6 wks as it takes this long for milk to get established, but between you, me, the gatepost & loadsa people reading this I expressed from end of week one. I actually had major latching problems & gave up bf'ing & expressed every three hours for 4 wks until I got the problem of latching sorted with the help of nct bf counsellor.
Bearing in mind I expressed very frequently in order to help my milk supply and my LO didn't have a nipple for 4 wks, she then took to me when I got the latch right no problem.
People do say babies can get confused with bottle and nipple but I never had a problem, some people say a lot of bottles in a day may cause issues and if the flow is too fast they prefer it as they can get the milk easier. These are all points to consider but do what you feel is right.
Some people I have spoken to have real problems expressing and gave up. Another lady I know had one side which was really sore & just expressed that side to give releif & a little healing time.
Don't forget, it will still be painful expressing, my toes used to curl when I was sore!
A couple of helpful tips to help expressing, I was told & used were to gently massage in small circles the fleshy part of boob, then gently stroke towards nip all round boob to help with let down & if further assistance is needed looking at a photo & thinking of baby.
I reckon, there's good and bad points but I'm confident you, like me will listen to advice and do what you feel is right.
Let me know how you get on and shout if you want anymore waffle from me!