Not quite U-pick, but you might read "
Ten Acres Enough" for a 19th century New Jersey berry farmer. Some of the points he brings up is that (a) you can make a living on a small piece of land because it's easier to manage, versus having a hundred acres that you can't manage. And (b) the most un-economical part of running a berry farm is the packaging. Back in his day (1840's-1860's?), they would use woven baskets that would require a deposit and a return. He predicted that someone who invented packaging sturdy enough to protect the fruit but cheap enough to be given away with the product would revolutionize the economic feasibility of small fruits farming. And to this day, packaging really is a hurdle for all kinds of small-farm mom-and-pop-type agriculture, whether it's eggs or milk or apples or berries.
A third thing he mentioned--- from the times before shipping your fruit in from around the world or from force-ripening stored unripe fruit--- was the economic importance of getting the best prices with the earliest fruits. So, for example, if I can expect my apples to be ready for harvest between late August and the end of September, if I can have apples that are ripe in late July or early August or even mid-August, I can beat out my neighbors' product and demand higher prices because there's no competition. However, as I've found out with my own trees--- early fruit isn't early fruit because it ripens/develops faster, but it's early fruit because it blooms earlier. So one side effect that I've found with my trees is that in its effort to put out its flowers two or three weeks earlier--- it also has a greater risk of weather damaging the blossoms. It might be a wind storm that knocks all the flowers off, or a late ice storm that freezes them. So even if the tree variety is suitable for my zone according to what the USDA zone map claims I should be able to handle--- Mother Nature doesn't care what the USDA thinks, and does what she feels like. So there are years where I don't have peaches or plums or apples because March roared in like a lion.
Another thing I've noticed with my trees is that they don't bear regularly. So if I have plums, I might get 90 lbs of plums off two trees one year, but the next year, I might only get 40 lbs of plums. Or if I have pears or pecans, they tend to have a year-on year-off cycle. So you have good years and bad years, but I don't know enough to have control over how it works out.
Fruit trees also tend to be irregular when it comes to lifespan. At my old house, I had peach trees that the previous owner had planted. She died four years before we bought her house, and then lived there for another six years. And we left that house fourteen years ago. So those peach trees are at least 25 years old, if not more... they're still alive. I don't know how they bear, but they're still alive. Whereas I planted a Jonathan and a Winesap dwarf tree at my current home about five years ago, both at the same time, and they decided to die this past fall--- after getting through all the heat of summer and they were now comfortably in the fall, nothing too stressful going on, just poof, they died. So when I read about people with hundred-year-old orchards, I'm curious as to how they get their trees to live so long. Dwarf trees supposedly live about 15-20 years, but even with water, hay mulch, crushed egg shells, and bunny poo, mine only made it a fraction of that long.
When we have a mild winter, I'm uncertain about when to prune my fruit trees, because I'm never sure if they're dormant enough for pruning. But the best apples usually grow on two-year-old branches. But pruning helps light and air reach the fruit.
With my peaches, sometimes it's funny, because they'll ripen, except where the shadow of a leaf is covering it, and in that one spot, it will have a leaf-shaped unripened spot.
Sometimes it can be hard to figure out when something is ripe or not. But if I wait for it to ripen on the tree, the ants will climb the tree (especially for my cherries) or the birds will get them. (At least, my husband tells me the birds are eating my fruit. Chapter 15 of Ten Acres Enough makes me wonder in the back of my head, but not enough to argue.) Other times, I use the un-ripe-ness to my own benefit--- I like making plum cobbler. If I make it with my plums in June, it tastes like a tart cherry cobbler. But if I harvest my plums after the Fourth of July, they sweeten up a lot.
Even though I like small, compact trees like dwarf trees, because it makes things easier to harvest, I tend to have my trees near the street, and a lot of my fruit at human-height tends to disappear.
You might do an Interlibrary Loan for Intensive Orchard Management: A Practical Guide to the Planning, Establishment, and Management of High Density Apple Orchards to help you with your daily/weekly tasks. Otherwise, the purpose of your apples is going to affect how you manage your orchard--- a section of orchard meant for cider apples will be managed differently than a section meant for eating apples or pie apples. But for U-Pick, you really want to have a staggering of different varieties (and perhaps different fruits) so that you can maximize the number of months you're open to the public. So, for example, in my area, strawberries are available early April through early June; blackberries are mid-June through mid-July; and grapes are mid-July through mid-August. At a different U-Pick farm in my area, they concentrate on vegetables-- they have 11 different kinds of vegetables available in the spring; nine in the summer; nine in the fall with a few sub-varieties mixed in; and three in the winter. But they don't necessarily commit to having anything specific in a certain part of any given month--- you need to call ahead to ask how the tomatoes are doing, if you're wanting tomatoes, and then they can advise you on the specifics. Communication in general is important--- we're so used to going to the store and getting what we want, it can be a surprise that something's out of season, something got attacked by bugs, something didn't make it through the heat, there was too much or too little rain, something got eaten by deer, or someone came by yesterday and picked a gazillion buckets of exactly what we wanted, and the next round isn't ripe yet.
A lot of the U-Pick type farms in my area also participate in CSA (Community Supported Agriculture) boxes. So you might have a few dozen small farmers collaborating with the CSA--- one person might be a dairy; another might have eggs; another might do fruits; someone else might do honey; etc. They also get supplemental income from farm tours, homesteading skill-type classes, farm-to-table dinners, or other things. Some might allow part of their land to be used for RV parking, glamping, or whatever.
