You can (and should) do all that. However until you actually disconnect from the utility power you don't know for sure that the systems all work. The generator powers a load, but turns out your hospital is more load than you thought. Or the generator starts but the switch to connect the hospital to the generator is broke and you didn't test that...
In the end you WILL test what happens when the hospital plunges into darkness. Would you prefer the first test to be a a bright sunny day when all the staff is ready for something (and you can turn the utility power back on quickly if something fails), or when someone with a backhoe/chainsaw has an accident with your power feed. The latter will happen, I don't know how or when, but at some point in your future trees will take down power lines, backhoes will cut something, major weather events will take out power for days, maybe a large blackout...
You should have course test everything separately often. However if you wouldn't let a random electrician (electrician only because they will know how to not kill themselves) turn off your utility connection with only a day of warning, your system isn't trusted to handle real events which are typically much worse than a clean turn off the switch.