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I think regardless of the block, if it's something he'd like to do, then take him.
I once took a mate in on the coast, pushing 120kg and unfit. After a day or two of sitting around he got out on the hill with us and had the best hunting experience hes ever had. Shot a 13 inch bull on the last day, a couple kms from camp and it's now on his wall.
Another option would be getting dropped off in the Landsborough somewhere outside of the wilderness area. There are some nice flats and bush edges to hunt, the river and just a mean place for a holiday in general. If he got itchy feet, a day up into tahr country is quite feasible.
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Go to any valley with a low scrub belt that has had heavy helicopter shooting pressure. Get up real early and they will be coming off the tops from feeding at night to bed down in the cover of the scrub. Likewise with last light in the evening when they head back up for a feed. I imagine there is a good few valleys that will fit that description as of this year. Take a fishing rod for the middle of the day. Have fun!
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With all this talk of him shooting and you retrieving, perhaps you should get him out to a couple of field target shoots. 14 months is a good amount of time to sort out gear like rangefinder and trajectory and any eyesight issues. Contact gillie and organize to go to his shoot at tarata in the spring. They had a hunter class course there and it's about 2km of walking on farm tracks. Also taihape branch have a nice shoot which would be within a long day trip distance. The preparation will be as much fun together as the trip itself.
