You shouldn't need a head support in the car seat - they aren't recommended anyway from what I've heard.
As for the pram, I haven't used that pram myself, but head supports are good when bubs is still tiny and the pram is semi-upright. I used one with DS1 when he was tiny and hated lying flat in the pram. I raised the seat so he was slightly upright and used a head support then.
I have the citi mini and i would probably recommend one for when bubs is little, just for extra secureness. We have a pram liner in ours too but only cause the fabric is so pretty i dont want to dirty it lol
We have a baby jogger city select (double) and have lambskin pram liners for both kids plus a head cushion thingy insert for the bub to help support it's head a little
Yes, you can still pull up the handle even though mine covers it. I just slip my hand under the liner to pull it up. I actually took my liner from my Phil and Teds lol. I got it made at minihappyme dot com they also do ones for baby jogger but cause i already had one for my doubles kit i tried that and it fit ok. I found the infant head support good for the capsule too.
Oh, i just realise that you wont have a capsule, the carseat should be fine without one. Maybe just get the pram liner (cause they are always handy esp later when bubs is eating in the pram and things get dirty and makes it easier to throw in the wash rather than sponging down the whole pram) and when bub arrives if you think you need a head support too then get one then. The pram liner does give quite an extra bit of padding.
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