I'm kind of working with a 5 year plan (includes this year).
Rest of this year:
Fully prep garden areas (fencing, soil prep, etc.), soaker hoses, row framing, etc.
Build out bunny stall (converting one of the horse stalls for the bunnies)
Rig some lights on chicken coup and in hay storage shed
Get a good diesel generator (at end of storm season, may find a deal)
Dakota driveway alarm (existing one kind of sucks)
Redo garage/workbench station (and with a Faraday cabinet for power tool storage, along with other electronics)
Keep replacing all light bulbs with LED (use less power)
Build good-sized doghouse in dog yard
Freezer chest for more frozen food storage
Walling up the glass doors from back porch (ManCave) to living room (mostly for wall space, but also removes this weak security issue).
Next year:
Grow gardens (starting in Feb) (both food gardens and medicinal/herb gardens)
Add another riding horse
Antique sewing machine (probably get this sooner, if we see a good deal)
Put in Koi pond (after cold weather is over, and after gutter system in that area)
Plant fruit trees (apple, orange, pear, avocado) and bushes (more blackberries and some blueberries)
Get more rain barrels and gutters to feed them
Put in an above ground pool (for fun, but also more water storage) and deck around it, including grill station
Install manual well pump
Camera system with 8 cameras
Build concrete planters (that can be dug out to be sentry positions)
Secret door bookcase to bedroom (mostly really for book storage than security, but just a neat idea and the location is perfect for it).
Inset vehicle stopping posts along street-facing fence (every 4 feet, 6 inch diameter posts, 2' out of ground, 2' in ground)
Add goats to the menagerie
Following year:
Solar powered well pump
Solar powered entry gate (more for convenience than security)
Start augmenting some items with solar powered options (especially in stables and garage).
Fuel storage tanks and pumps
Convert utility hall for food storage (will have home-canned fruit/veggies), revamp pantry and some interior closets as well.
Start on improved fencing (higher and newer fencing in back and sides of property)
Put in small bathroom for stables (this may be more of an outhouse style, have water running there, but not sewage yet)
Get more oil lamps, lamp oil storage
Expand chicken coup, add roosters and incubation area/equipment
Get more bunnies (use breeding area of stall conversion)
After:
Increased use of solar power, with goal of eventually being able to go off grid completely (although with reduced power use if doing so) and still have AC, appliances, etc.
Get enough inflatable mattresses to convert stalls to bedrooms if needed (along with more bed linens)
Amass more building supplies for repairs, converting stalls to living areas.
Amass more medical supplies, equipment
Increase food stores (dry goods, canned meats, powdered dairy, etc.)
Amass spare key auto parts for existing vehicles
Increased water storage tanks
Old school crank radio stations around ranch
Continue to redo fencing (add barbed wire to sides and rear once all is at 8' height, you really don't see these fences from the road, so no eyesore. Plan is to have the materials to then add to front fence post SHTF).
I'm sure there are some minor things I'm forgetting though.