Personally I would do your automations in Node-Red. I was reluctant to go down the NR route but finally bit the bullet a few months ago, and do not regret it. I was able to combine 17 different lighting automations in HR into one flow in NR. NR makes it easier to see everything in one place, if you take the time to set it up.
For setting up your automations, it depends on what sensors you have.
The most important, from what I can see, is the ‘transfer switch state’ which would equate to a ‘we have a problem’ state or ‘power outage’ state.
My generator starts 15 seconds after loss of power and switches over to the running generator when it is ready, after power restored and stable for 1 min it transfers back to line and shuts down the generator. I have an input of ‘transfer switch state’ but also of ‘power outage’ which will indicate slightly before the transfer switch.
If any of this integration of yours to your generator utilizes any cloud based data, then it will not always work; if it is local then you should be golden.
When I lose power, I also lose water. Water is from separate power than my house, so can not power from my generator. I have an 1100 gal water tank that I have ‘automated’ to cover these situations. Power goes out, generator starts, 5 mins after power outage my shallow well pump starts for the tank, 30 seconds after the pump starts then a valve opens to supply water to the house (check valves in place to prevent circulation and sending back towards the ‘normal’ supply). After normal power is restored then after a minute the valve shuts and 30 seconds later my pump powers off.
Things of note: you HA instance will need to be on a UPS and so will any WiFi routers or any other device you use to monitor or control your automatons. The actual devices you want to control don’t need to be off a UPS but the backbone absolutely does unless you don’t mind the delay in HA restarting any everything reconnecting (then you need to account for that in any automation).
I also have some lights that turn back on after power outages, and I have an automation to turn them off after a period of time unless there is motion detected in the area where they are.
It is also extremely important to note that if you have ‘smart plugs’ that you are using to monitor equipment that you have there power restore state set to what is appropriate for that device. For example my deep freezer is on a smart plug and on power restoration it returns to an ON state. Fans on the other had stay off until manually reset; I could (and do) automate some restoration after return to ‘normal’ power but there are reasons to wait to manually restore some items (depends on your circumstances).
I also send a notification to phones (mine and wife’s) that power is out and status of water. So if there is just a power problem and we are not home and the internet still works then we get notified. I do have a sensor for internet status but have not made an automation for notification when internet is restored (I did forget about this, so I might work on that tomorrow).
So, I did not actually answer ANY of your questions, BUT I did give you something to ponder.