First thing coming to mind is to discover what other gardeners have had great success with locally.
That list will vary a lot depending on where you are.
Go for low maintenance fruit trees, as per the book Tree Crops by J. Russell Smith.
In my area that gets down to mulberries, figs and persimmons.
https://archive.org/details/TreeCrops-J.RussellSmith
I'm currently experimenting with dwarf versions because I'm working with less than an acre.
Best so far are World's Best Mulberry and Fignominal fig.
Persimmons are a bit trickier to get going. If you want dwarf varieties you'll have to raise American Persimmon rootstock and graft on Asian scions...or buy them ready to go.
I have access to a REALLY good American Persimmon (they are quite variable in quality, some need cross pollination and some not) but they grow huge and I just don't have the room and I'm old so the time to grow out rootstock and select doesn't appeal.
https://floridafruitgeek.com/2019/11/28/the-turkey-lake-american-persimmon-free-fruits-scionwood-are-available-in-gainesville/
Root crops would be the second thing coming to mind. Everyone else covered that very well. Again, good local stock makes a difference here, and so does experimenting with different varieties.
I've grown a purple sweet potato bred by a guy over in St. Augustine FL that seems to be both quite bulletproof and tasty without the involved pre storage rituals. I crate 'em then put them in storage.
Murasaki is another one that does above and beyond here.
Particularly the ones I can buy from the local discount grocery for a little over $3 a pound.
https://martianpotatoes.com
Kuroda carrots do above and beyond here.
The Japanese turnips are tasty little things as well as growing well in winter here.
https://www.rareseeds.com/store/plants-seeds/vegetable-seeds/turnip-seeds
Daikons are bulletproof. They use them locally on farms as a cover crop.
I'm trying this this winter, attempting a cover crop that outputs food. Growing nicely so far but the jury is still out. My mix on this was kale, turnips, chard, sugar snap peas, oats and winter rye grass. If I've figured this correctly it should mostly self terminate once it gets hot.
https://blog.nutri-tech.com.au/cocktail-cover-crops/amp/?
I have an inexpensive 10' x 35' greenhouse built from 8' steel t posts, frames of those carports you see everywhere, fence wire, and inexpensive greenhouse plastic from Ebay.
This keeps me in tomatoes, cukes, peppers, seed starts most of the year (the heat here becomes an issue in the summer) and is just a great addition.
Automated watering happens via buried 40 gallon totes, fountain pumps, timers, and a tubing network of the irrigation stuff I use otherwise.
I hand watered it the first year and that got old in a hurry.
I run hydroponic solution in it but you could do it with organic ferts and water instead of the nutrient solution.
I also grow things in containers and grow bags in kiddie pools to keep them watered. Mostly kale, chard and onions in these for the winter.
I'm too flat for effective swales but have plastic lined trenches wide enough to hold bigger nursery pots which simplifies keeping all that watered.
Some day I'll try the Bill Mollison's gley technique, making an anerobic slime to seal trenches and swales to see if I can do away with the plastic.
https://simplingforall.blogspot.com/2015/10/gleying-pond.html