My power system is also layed out such that in interlock won't fit the bill. Main breaker is at the house, generator feed is at the barn, which is fed from the house. Things are clearly marked, wife and oldest son understand the process and order of events clearly. We likely have a better understanding of the safety risks than most, as I have 20+ years of electrical background, and have installed many very nice back-up generator systems with auto-transfer switches, and hope to have my own someday.
The point I state clearly, every time we have a power issue, is turn off the main breaker FIRST, and save the life of the guy out in the cold/rain/snow trying to fix the power outage, then go to the barn and hook up the generator, start it, and very last turn on the breaker for generator feed to the barn panel.