I was a fruit tramp (i.e. migrant worker specializing in fruit) for eight years, from 1974 to 1982. I started with cherries, usually in Washington in June, but one year I started in Lodi, California, in May. Then came the Columbia Gorge cherries - first White Salmon and then Hood River. After that came the late cherries at Flathead Lake, Montana, peach picking, pear picking and then the apple harvest. By the end of October I was done picking and took a week backpacking trip in the Pasayten Wilderness west of Loomis, Washington. I always carried winter gear and some years I used it - other years I hiked in runners and shorts. Then back to Tonasket to prune all winter (for three years) or later, off to Vail to spend the winter ski-bumming.
Now I have my own farm and orchard and I keep my trees short enough so that I can pick them with an 8-foot ladder. On the tramp, I had to use 14-footers for the pears and 20 foot extension ladders for the cherries. Most of my apple picking was on 10-foot or 12-foot ladders. Today, as I look out my office window, I can see my orchard and the ridge to the north of us. Up on the ridge to the northeast is an old single-wide trailer that is still used. Straight north is a building site and a storage unit that might as well be another trailer (in fact there was another old single-wide up there until last year when the new owners towed it away). My trees partially hide the trailer now and I am thinking of letting them grow another two feet so they will completely obscure the trailer and any building that goes up on the building site. I have been encouraging apical dominance in my pruning the last two years and the tip growth on top has been good. I was intending to shorten the tops a little this year to encourage bushiness, but now I am thinking of letting them go and getting a bigger ladder. This is problematic, as I am older and less sanguine about slamming into the ground at 32 feet per second than I was 30 years ago. There are pluses and minuses. I like to look out my window and just see green. That will probably carry the day.