I just wanted to follow up on this thread I started to say thanks to everyone - every response was helpful to me and I always enjoy hearing how others manage their setups.
Unfortunately my conclusion is that, unless you're on a flat 5 acre field like I used to be, you ideally need a collection of vehicles to manage all the task appropriately.
Since I have a Yamaha Kodiak ATV and my neighbor has a 500CC snowmobile, I am increasingly thinking my next major purchase will be a 25-30HP tractor. As I noted in my first post, having just bought a new (bigger) place and still having young kids, I need to invest in something that will make my jobs easier all year round.
While I have 50 buckets I'll put up this year on a flat top in the back corner of our woods, my long term plan is to run tubing down the edge of our 30 acre parcel that follows a long drainage / slope to a gulley just behind where I want to place a 16x24 sugar shack. I think I could probably pump right from that collection spot, up a hill to the eventual site of a shack.
I would still run a couple dozen buckets because I love the nostalgia and my kids enjoy tapping > hanging them but I could probably be choosy about where they go to make collection easier.
If/when I make the final new purchase I'll let you all know. A local ag retailer has both a used 2019 Kubota 4x4 26hp and a fully kitted out (cab, hydraulic plow, power dump) JD 825i XUV for about the same money ($14k~).
We shall see!
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2015: 8 bucket taps (7 red, 1 sugar) on DIY barrel evaporator
2016: 13 taps (bucket and tube) on block arch and hotel pans
2017: SAME
2018: 25 taps on 2x3 flat pan and resurrected barrel arch
2019: 25 taps...same setup plus DIY 3x150gpd RO filter
2020: 50 taps, all buckets..."new" oil tank arch setup
2021: 100 taps (50/50 buckets/3-16 tubing) on 2x4 divided pan
2022: 150 taps (50/100 b/t) on 2x4 pan with sap warmer pan
2023: SAME
2024: 150 taps, added single-post 4x40 RO system