I think the larger quantity you boil the more closely you need to monitor it as it nears a boil, regardless of kettle size.
I use my 4 gallon kettle (from my concentrated-wort-boil/extract/stovetop days) on the stove top as a mini-mash tun with a huge nylon grain bag. The most I've mashed in it is 6.5 pounds of grain in 3 gallons of water and that is about 1" - 1-1/2" from the top. That grain bill goes with 6lb DME for an approx 7% ABV finished beer.
So I mini-mash in that on the stove while I bring another 4-5 gallons, depending on my mini-mash volume, to a boil in my 9 gallon kettle outside on a LP burner stand (Bayou Classic SP50; highly recommended). Once the water boils, I add the bittering hops, turn off the burner, add the DME (4-6lb per recipe), fire the burner back up, and watch that thing like a hawk with my hand on the throttle. Even with 5-7 inches of headspace, it will go Vesuvius all over my back deck. (My power washer got a workout the first few months I had this setup.)
So, when the mash is done, I pull the bag of grains above the wort in the kettle and slowly rinse with 1/2-1 gallon of hot tap water, dispose of the grains, and put the lautered wort back on the stovetop over high heat and bring to a boil as a mashout. Then I dump that wort into the wort that is boiling out in the big kettle. I actually have it timed pretty well where I can start the mash, set up the big outdoor kettle and get it started, lauter/mashout, and get the mini-mash wort into the big kettle as it comes to a boil.
I do keep a stock pot filled with water simmering on the stove to add to the big kettle if I need more volume at the beginning of the boil. I've found that if I start with a 7 gallon overall volume in the 9 gallon kettle (which conveniently enough happens to be at the handle rivets), after a 60 minute boil I end up with right around 6 gallons, which leads to 5.5 gallons in the fermentor, and 5 gallons in the keg. Your system's boiloff rate will differ, of course. I do have the quantities in my recipes compensated up for the 6 gallon finishing volume.
Man, War and Peace over here... I think I got it all.