John Schinnerer

Oats will do...
And, rye will give you considerably more root depth and total biomass, below and probably also above ground.
However probably won't winter-kill, this link from University of Vermont mentions using oats instead for that purpose:
https://www.uvm.edu/vtvegandberry/factsheets/winterrye.html

A bit more on rye:
https://soilandhealth.org/wp-content/uploads/01aglibrary/010139fieldcroproots/010139ch6.html

A classic biointensive compost/cover crop mix is winter rye, winter wheat, vetch, and fava.

I can vouch for this combo in the Pacific Northwest from when I had a biointensive garden in Seattle. The rye for sure produces a LOT of root mass, and deep.
None of it winter-kills in that climate of course. Which is good if you want max biomass for compost, but your case is somewhat different if you want the reduced work from a winter-kill.

Mr. Lawton is a bit late to the party. John Jeavons researched this as much as 40-50 years ago in the Ecology Action research gardens. His focus was of course on temperate climate annual crops, grown French Intensive/Biointensive style. Different options in other contexts - context is everything. In the temperate-climate intensive horticulture context, Jeavons claims, for the labor required vs. calories and nutrition gained, as well as space required (outputs per area of input), grains are not very efficient, a relatively poor choice. Beans (dry) are not so great either, in terms of output per area of input. By his findings, potatoes win hands down in that context.  Especially in that they provide both significant calories and significant nutrition in less space than most other crops, not a very common trait in human food crops.

If you're subtropical or tropical (ST/T), yes there are paddy-rice-based cultures aplenty. But there are also multiple tuber/corm based cultures, Kalo (taro) being a primary example in parts of SE Asia and Polynesia, definitely Hawai'i (where it is a crucial element of the human origin story). Sweet potatoes, as someone mentioned, are another efficient ST/T staple (and yams). And in other parts of Polynesia the tree crop of 'Ulu (breadfruit) is the dominant staple. Cassava also comes to mind, mostly for ruggedness and ease of cultivation, and primarily for calories, as it's not all that nutritious. And lest we forget, potatoes originated in the Andes...

The question of grain, storage, & surplus is an interesting one...given that some systemic analyses of human history common in permaculture contexts suggest that it was our shift since ~10K years ago to increasingly large scale, sedentary, reduced-diversity grain agriculture, with its accumulation & storage of surplus, that increased our ability to overshoot population-wise, and also enabled emergence of warring nation-states. Allegedly the oldest written human records anyone has found to date were all accounting - military accounting, and grain agriculture accounting.

Puerto Rico is a territory, not a state - I'm assuming the original riddle-poser meant states only?
If we are including territories, it would be Rose Atoll, American Samoa.

For the extreme points of the USA, Hints here:
https://en.wikipedia.org/wiki/List_of_extreme_points_of_the_United_States

There are a few tricks here...Alaska (the Aleutian island chain part) crosses the line from west to east longitude, so it is both the western-most and eastern-most state (sorry, Maine!).
And also the northern-most.
A hat trick for Alaska!

Fascinating...I would add to the topic line:
Australians also please don't use two-letter state abbreviations... :-)

At least not when referring to WA...Western Australia, that is. Two of my virtual colleagues are in Australia, one in the self-same WA, in Perth area. There's no Perth in WAshington state, USA, though there is a Perth in NeVada, USA, and in NewYork, USA.

And for VIC, the abbreviation may be better.. spelling it out may leave one wondering, is it the state in AUS or the city in BC, CAN?

For country names there is an ISO standard for three-letter abbreviations that are unambiguous: https://en.wikipedia.org/wiki/ISO_3166-1_alpha-3

As to the metric system...it's theoretically been the preferred system of weights and measures for United States trade and commerce since 1975, according to United States law (the Metric Conversion Act of that year). The scientific and medical domains use it almost exclusively, among others - our money system is metric, and we use the metric second. But not USA society in general - not everyday stuff like fuel, groceries, hardware, furniture, building materials, a vast variety of everyday objects, etc.

My theory is that the USA failed to convert because we tried to be too 'nice' about it. The idea was "a carefully planned transition to the principal use of the metric system over a decade." (quoting Wikipedia).
Those of you old enough will remember that questionably designed effort - signs everywhere in both systems, causing both confusion and extra expense; lots of politely encouraging PSAs (oops, another acronym, Public Service Announcements) telling people how to do the math...and that's what killed it, the timeline and the math.

Other countries mostly just said "on this date we switch" and everything changed, the cubits and rods and furlongs and pints and tablespoons and drams went away, the meters and liters came in, and within a couple weeks or a month at most everyone was used to it.
But ten years? And math? Doomed from the start.
The huge irony with the math part is that it's waaaaaay easier in the metric system.

+1 and another +1 to the comments about quality of work and details of installation. Makes all the difference. Especially the one about materials overlapping correctly (flashing, roofing material, etc.). If that is done right it will not leak, even with no goop at all. If it's done wrong it will leak sooner or later and no amount or type of goop will permanently stop the leaks. Only taking it all apart and putting it back correctly will.

Also +1 for clerestory windows as another option. Mainly regarding being easier to install correctly, and, if under adequate eaves they won't leak even if installed poorly, just because water never hits them. Plus good for low-high ventilation flow if climate makes that desirable in some season(s). And can do that even when it's raining, if eaves are adequate. Skylights on the other hand usually have to be closed to keep rain out.

Note that any window up at top of a wall will lose more heat than a window lower down (because it's warmer up there and all else equal), so a clerestory right under the eave and a skylight just a bit up the roof will not see a huge difference in heat loss. Plus you will need more surface area for the clerestory in most cases to get the same amount of light as a given skylight.

If zero roof penetrations is easy and doesn't conflict with other important design parameters, sure, go with that. But I would not shut out beneficial and/or desirable design options that involve roof penetrations just because poorly done roof penetrations may leak. I would instead make sure any roof penetrations are done properly.

If you live somewhere with longish darkish winters, absolutely consider human need for natural light in dark times a design parameter. It's part of our health care. Especially if you are prone to seasonal affective disorder (SAD) or anything close to it. It is amazing how much 'better' (healthier) a closed/dark/gloomy space can be with some additional natural light, even (or especially) in mid-winter.

I used five gallon  bucket soaking for quite a few years when living off-grid in Hawai'i.
There is no need to do much (thoughtless and protracted) labor. The absurd amount of laundry labor you read about historically was mostly culturally imposed, not required to clean the clothes.
Soaking for ~24 hours, the water (an ultimate solvent) will do most of the work, in clean water with some soap in it. Put clothes & soap in, agitate by hand for a few minutes, come back 24 hours later. Or agitate a few times briefly in between if you want.
There's a book I've lost the title of, by an Amish woman decades ago, who says all this.

If you want to stack some functions, try something like in "Travels With Charley" - the protagonist puts clothes, water, soap in a 5-gal bucket with sealable lid, secured it in his vehicle, and driving (partly unpaved) to town for errands & supplies gave it plenty of agitation.

Ditto comments about not over-packing the clothes. Like cooking pasta, too little water is not good for the outcome.
Ditto the manual roller-wringer if you want to squeeze out max water with minimum effort.
Otherwise it's however much you can wring out by hand. Which, if you do it appropriately in terms of body mechanics/not hurting yourself, can be one or both of gym-free workout and emotional catharsis.
Also ditto the winter line drying outside works. If below freezing the water will sublimate (go from solid directly to gaseous form, skipping the liquid form) out of the clothing, unless you are somehow in an extremely humid but also below freezing context.
I've also used those great old style wooden collapsible indoor drying racks.

John Jeavons covered this topic well decades ago in his book "How to grow more vegetables etc. etc."
Speaking to annuals of course, which seems to be the main thread here. In the long run, yes, get perennials going!

A key point he makes that is hinted at in this thread but is not called out explicitly:

We need both calories and nutrition. A subsistence garden needs to work both parts of that equation.

So beans are a poor choice because they take a LOT of space for any significant amount of calories, whereas potatoes (or similar for other climates, e.g. yam/sweet potato, turnips, cassava, taro/kalo) provide lots of calories in a small space.

So calories needed from veggie crops have to be covered. You can have great nutrition but still starve if not enough calories.

Then look at nutrition per crop - cassava doesn't have a lot of nutrients, just calories, whereas potatoes, or taro, for two examples, are significant nutrient providers also (if you are at least subtropical and can grow taro you are blessed, you can create a large amount of calories and nutrients in quite a small space).
So some calorie crops are also nutrition crops, and some not so much.

And, just for nutrients we may, or will, need to grow some things that aren't calorie-efficient per area used, but we need them anyhow.

Once calories and essential nutrients are covered, then cultural preference and habit and so on can be catered to.

Another key point he makes is that none of this accounts for oils, which we use daily without thinking much of it, but are very challenging to produce at small scale.
And then he reminds us about spices/seasonings, which add to the complications of producing anywhere close to what we are used to eating daily.