Oh I really feel for you.. It was a nightmare getting to feed DS1 (took him 10 days to latch on) made a great difference to how I felt about him and generally the our first 2 weeks together was stressful and quite unpleasant. However once he did it we never looked back I fed him until 10-11 months.
So 2nd time round I had the same apprehension as you have, I thought carefully about the first 2 weeks and tried to think about things that may or may not have worked for me. I realised that we actually managed to get him to latch the first day Dh went back to work we were on our own and it had to work..
So I told midwife all about our trials from first time and asked if she would let me try on my own.
WOW totally different baby I tentatively sat down got out the boobage within 10 minutes of him being born, and he was like a baby bird mouth wide open very hungry and he just knew what to do.. In every way they boys have been different, you may find it will be the same for you.
Let your midwife know you want support and try it.. you never know,, could work like a dream
I am sure there are ladies on here who can offer more specific advice, just wanted to share my experience hope it gives you some hope.