If the goal is to take "has never even read the wiki!" And turn them into "Losing is FUN!", then you will need to start with the simple, and work up. Ideally, you will cover the most basic functions first, and reiterate those things regularly.
Things like loo(k), (v)iew, conten(t)s, (c)reatures, (d)esignations, and all that.
Something kinda like this as an outline.
"Welcome to Dwarf Fortress!"
Movement keys
Pause key
Loo(k) menu
Look screen information and details
Inside vs Outside / Light vs Dark
Stone floor vs soil
Water depth
Look window for creatures
(V)iew menu
View menu information and details
View a dwarf
General page
Thoughts and prefs page
Inventory
Wounds
Labor and service page
Overview of labors
Assign labor to 1 of the starting 7.
Segue into the (c) menu
(C) menu
Dwarves
Viewing preferences/thoughts
Assigning labors
Cancelling certain jobs
Intro to the manager window
Livestock
Deceased
Others
(Z) menu
General information
Broker & appraisal (Segue to the nobles screen)
Kitchen
Livestock
Stocks
Crime
Stone
(N)obles screen
Assign book keeper and broker
(Requirements screen, overview of nobles, demands, and mandates)
Con(t)ents menu
Look inside the wagon
(Q) menu
Deconstruct the wagon
Saving and loading
"My first fortress!" Part 1!
Fundementals of fortress life
Shelter
(D)esignate menu
(T)rees (for beds)
(P)lants (surface crop seeds, bolster supplies for booze)
Downward staircase
Upward staircase
Mining basics (dig a simple phase 1 fortress)
Channeling (get fresh water from stream/brook for well later)
Advisory about minding where and how you channel
Advisory about water pressure
Infotainment about stone, soil, metal core, gem clusters, etc.
Stock(P)ile menu
Food stockpile
Stone stockpile
Wood stockpil
Bar/block stockpile
Gem stockpile
Cloth stockpile
Furniture stockpile
Finished goods stockpile
Refuse stockpile
Certain items in refuse stockpile rot!
Custom stockpile
(Q) menu on stockpiles after placement
Necessities of life: booze, food, masonry, security, trade
(B)uild menu (just the basics for now)
Build an underground farm plot
*Notes on seasonal restrictions on underground crops
Plump helmets
Pig tails
Cave wheat
Sweet pods
Quary bush
Dimple cups
*Plant plump helmets to secure reliable food supply
Build an aboveground farm plot
*note lack of seasonal restrictions
*note primary source of surface crop seeds is the (p)lants option in (d)esginate menu
(Plant wild strawberry/prickle berry for alternate reliable food/booze source)
(Seed stockpiles for efficient planting activity, and customized food stockpiles for seed management)
Mason's workshop (use raw stone, or wood logs)
Make stone blocks
Make stone tables
Make stone chairs
Carpenter's workshop (use stone blocks)
Make wooden beds
Make wooden barrels
(Optional) make wooden bins
Still
Brew drinks
(Observe seeds going to seed stockpiles, booze going to food, etc.)
Beds
Create communal dormatory.
Brief blurb about military dorms, and dedicated civilian housing, vs communal dorms-- pros and cons
Craftsdwarf's workshop
Intro to trade goods
Farmer's workshop
(Quick blurb about grazers, the act(I)vities menu, animal requirements from the wiki, and wool production. Suggestions about how to keep grazers, which grazers simply can't be kept because they can't eat enough to stay alive, etc.)
(P)rocess plants
Pigtail fibers/ropereed fibers, and seeds being produced- thread goes to cloth pile
Shear an animal (if available)
(Wool goes to refuse pile, and will rot if ignored!)
Spin yarn (if available)
Yarn goes to cloth pile
Loom
Weave cloth (plant fiber)
Weave cloth (yarn)
Weave cloth (silk) -- brief blurb about silk and silk farming, more details later
Clothier
Seeds and bags, a brief education
The dangers of nakedness, and why clothing needs to be made
Essential clothing: shirt, pants, shoes, socks
Trade depot
Brief blurb on trade
Architect labor
*wait for end of first year
Merchants and diplomacy
Migrants
"My First Fortress!" Part 2: Security
Overview of threats to a fortress
Dealing with said threats
Traps
Cage trap
Weapon traps
Pressure plates and levers
Mechanic's workshop
Stone mechanisms
Bridges
Caveats about size, and bridge function
Mechanics labor
Walls, (and the other constructions)
Military
Drafting military dwarves in the (M) menu
Setting up training schedules
Assigning weapons and armor
(Weapons, armor, and material choice considerations)
Creating training areas
Make armor stands, weapon racks, practice dummies
Place using the build menu
Use for military with (q) menu
Blacksmith shop
(Needs fuel, and metal bars!)
Wood furnace and furnace operator labor
Make charcoal blocks
Make refined coke (if coal is available)
Smelter
Producing metal bars from ore
Blacksmith (and smithy labors) part 2:
Making weapons and armor
Hospitals
Wells
Beds
Traction bench
The importance of soap!
Hospital zone stockpiles
Healthcare labors
Bowyer's workshop
Wood crossbows (comparison with metal bows)
Hunting labor on migrants, and managing bolts
Make metal or wood bolts
Animal training, domestication, and war animals
"My First Fortress!" Part 3: Home improvement
Bedrooms, and room quality
Wheelbarrows, minecarts, and pathing considerations
Construct phase 2 fortress layout
Dwarven happiness, tantrums, and the dangers of friendship
Burrows
Dining halls, zoos, statue gardens, quality furnishings, and room improvements
Friendships, pros and cons
Mitigating activities (brief overview)
The tantrum spiral, an overview
Warning about the loyalty cascade; don't murder dwarven merchants!
Dealing with, and planning for nobles, now and later
Peasant selection for advancement to count, thoughts, and rationale
Room placement and layouts, caveats about trap avaoiding in regard to diplomats and other considerations
"My First Fortress!" Part 4: Dwarven Science!
Magma is !!FUN!!
Magma related FUN activities
Basic magma tube breaching and magma workshop safety (magma crabs ahoy!)
Magma safety!
Magma safe materials
Floodgates
Pumpstack
Magma piston!
Magma cannon!
Minecarts are FUN!
Impulse ramps
Minecart shotgun
Normal payload
Water payload
Magma payload
Ballistic minecart cannon
Remote activated minecart hallway sentry system
Water is FUN!
Hyper pressurised water, for fun, FUN, and profit
Water cannon
Freezing variant in freezing conditions
Screwpumps cleanse nasty water!
(How to deal with nasty water effectively)
Science is awesome!
Obsidian machine! Who says stone is scarce these days!?
(Obsidian casting enemy elimination systems!)
Dwarven purpetual motion machines!
Pseudo random activators, traps, and fortress automation!
Vampirism, werecreature curses, and fun with contaminants
Falling objects, thrown objects, and other kinetic funtime activities
The atom smasher!
(Other funtime science, like the coinstar, dwarven eugenics, silk farms, etc.)
"My First Fortress!" Part 5: Hidden Fun Stuff!
<redacted> You KNOW what goes in here! </redacted>
"My First Fortress!" Part 6: addendum for anything else we missed!
Bear in mind that the above was a stream of conciousness produced screed, and is not by any means comprehensive- just a general idea for an itinerary.
Just add, remove, and shuffle around to make it more complete, and more orderly as needed, then make a script for yourself, and follow through.
Make use of the fact that snatchers, thieves, and siegers/ambushers won't come until after the fist year, and use the first year to cover all the basics of the interface, and deal with basic needs and security methods.