This is an awesome long-term plan — really well thought out, and it looks like you’ve already done a ton of homework. Turning 20 acres of mostly fir timberland into a hedged homestead is a huge project, but the phased approach you outlined makes everything feel doable.
Your Osage Orange hedge strategy sounds solid. The old weaving/laying technique really does produce an incredibly tough barrier, and in your area the deer pressure absolutely justifies putting the time in early. Mulching heavily at planting time is a good call too. When I work on hedge pruning in Seacoast NH, we see that young hedge trees respond dramatically better when competition from grasses is reduced, especially during the first 2–3 years.
A couple thoughts:
Companion plants:
For the first few years, I’d stick to minimal competition near your hedge. Clover can attract deer, but the bigger issue is that it pulls moisture that your young Osage whips might need, especially in a 20" rainfall climate. Once the hedge is strong and established, then start adding N-fixers and chop-and-drop species.
Coppice plan:
Your species list is great. Black locust especially will thrive and fix nitrogen for nearby trees. The “spray and pray” method honestly is realistic when you live that far away and have elk/deer issues. Locust and hazel are usually the toughest survivors.
Food plants (Phase 2):
Planting shrubs outside the hedge for wildlife is smart — it keeps pressure off the inside plantings. Serviceberry, elderberry, and chokecherry are good candidates that wildlife love and won’t need much pampering.
Housing (Phase 3):
Your RMH + Oehler-style build idea seems totally doable with the flat land you described. The drainage planning will be the biggest hurdle, but starting 4’ down and using built-in earth berms is exactly how folks in similar climates handle it. RMH in the greenhouse as freeze insurance is clever.
Overall, your plan is ambitious but absolutely realistic. The biggest challenge will be distance (only working twice per year), so anything you can do early on to reduce maintenance — heavy mulch, strong hedge establishment, and choosing resilient species — will pay off huge.
Would love to see updates as the hedge starts taking shape!