Changing to a 36t largest sprocket would have two effects/impacts.
1) It will give you a gear which is 6% lower so for a given hill this would allow you to pedal up at a higher ratio and higher cadence (spinning) and achieve the same speed (so at the lowest speeds - stay balanced).
2) Your rear derailleur will be at or beyond the limit of its capacity - you don't want the complication of the wolftooth link (or similar). And you don't need it with a choice of a smaller pair of chainrings.
By going to a 32t small chainring you have already gained far more (32t versus 39t implies a gear ratio gain (for going up hills) of 18%). If you go for the 48/32t crankset, I do not think you need the 11-36 cassette. The penalty is wider ratio between the gears as you shift in the middle of the cassette - a disadvantage for the ride you plan.
Going to a 48/32 crankset will mean you need to lower your front derailleur a bit, but the 16t difference between 48 and 32 is 'standard' for a normal FD (cf 50/34 or 52/36 cranksets) and the shifting should be fine. If your seat tube fitting is 'braze on' check you have the range to drop it (?3mm).
I'd just go for the 48/32 although frankly if you're going to keep the 11t smallest sprocket you could even consider a 44/28 (probably not available at a sensible price). My focus would be on the cassette. You have said that you rarely use the smallest two sprockets. Get rid of the 11t and have the small sprocket run as 12, 13,14 by a bit of customisation. I did exactly this for the Mille Pennines, which went up Hardknott Pass (at the 200km point) and up Rosedale Chimney (at the 770km point) -see
link. (NB the hills you're heading for are not that steep; they're long, and you may also have long stretches into a headwind.) I swapped my 12-27 cassette for a 11-30. But I then swapped the 11t for a 13t to give me a 12,13,14-30. On the cranks I swapped out my 30t (NB triple) for a 28t. This double action meant I was getting a gear 12% lower - 2/5ths from the chainring swap and 3/5ths from the cassette change.