wow ttm, i wish i'd asked yr questions when i started. I'm also a vest cardi combo wearer. And it is cool feeding when out if you've got moral support from dp/other mum, especially ni the early weeks.
Other things that helped are: our local sure start does a BF cafe, and that's where i first fed in public. And you get to see other people doing it and can stare with no weirdness and learn more about it. Also, do bear in mind always like theothers say that it does take time to get used to - HVs etc all said it taes 6 weeks for the supply to fully establish and for you to get like an old pro at it. And they were so right. I was suprised it took so long, and used to get so frustrated with myself. No need for that.
Another shock to me was how much time it took to do. Don't look for the benefits of ease from bf in the first few weeks. Just treat it as your main job - get yourself really comfy with a seat which is yours and all the pillows etc you need. This is so important as after a few weeks of not quite supported BF i ended up with agonising shoulder pains from muscle spasms tha needed physio to sort out. I always kept water to hand at my seat at home as well. Don't expect to lose weight apart from your pg fluid going, as to begin with BF made me ravenous. Insanely ravenous. So make sure you snack healthy and guilt free. My appetite settled down at about 2 months.
Finally with the MIL type issues, I was bombarded with well, not positive, BF comments by my mum and her sisters. The more we talked about it it though the more it boiled down to - they were brainwashed/frogmarched into formula feeding, and so have those lessons firmly in their head. Mostly they:
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couldn't understand the fuss about bf as 'my children were fine on formula' - when they see yours are too they'll back off.
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felt guilty they had ff and not bf - all these years later they had feelings of regret/anger/guilt that they needed to get past which time has done
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simply didn't know what the true benefits are, so education helped there
Most important one to get on side though is your other half. It's him who can make or break your attempt, as its him who will have to dive in to cover the rest of the housework while you spend HOURS establishing supply and technique. And its him who may feel left out by the intensity of your bond with baby.
HTH and PS - in my paltry experience, don't force yourself to establish expressing until you've got comfortable with BF on the breast. Expressing is another art form in itself I've found.