Looks like the second photo would be a better location in my mind. What size head tank are you planning on using?
A food grade pump would be ideal, Depending if you have electricity or are running off batteries/solar? There are quite a few options out there varying in price. I'm about to purchase a beer brewing pump with stainless components that claims to be able to pump 21ft of head and 7gpm.(Which i'm sure will slow down at that kind of height) That would certainly save you a lot of effort of moving buckets into the shack and justify the $200 price tag.
6th season solo sugar maker in a young sugar bush of mostly red maples
320 taps
2x6 self built arch, Flat pans w/ dividers
New 12x16 sugar house
CDL hobby 250 RO