So, I would use the ladder and do it yourself, but i would be EXTRA cautious when doing it. I personally know 2 people that have died at their homes from falling off a ladder (ice damn in the winter - looks like ladder slipped on their front walk, and another was trimming a tree in his yard because his daughter was getting married there within a few weeks). My uncle fell off a ladder measuring for gutters in front of his friend's house and ended up with a severe TBI and in a coma for ~4ish months, and it has now been 1.5 years later and he still can't function as an independent adult. Ladders are not good.
So, with all that said, we probably all know people who get in car accidents and die too - but that doesn't stop us. So, I would not pay the $400, but I WOULD be extra cautious with the ladder. Wear a helmet - you might think you look stupid, but it could save your life. Wear a helmet.
Move the ladder frequently, and ensure it's stability, and hold the ladder for your husband while he is on it so it doesn't fall. Do not let him reach far out so you don't need to move the ladder as often. It may take an extra 10 minutes of climbing up and down the ladder if you don't reach out as far, but you'll be far more stable. You might get bored holding the bottom of the ladder for him for hours, but think of how much more work you'll have to do if he dies or ends up paralyzed. Hold the ladder for him.
This is maybe less of a concern/possibility when on a ladder, but whenever i'm on the roof doing something (cleaning gutters, trimming trees,etc) I always try to think of an exit strategy if i fall. Sometimes there isn't a good one, but if you're going to fall, i would rather not land on a pointy lawn ornament 25 feet below me, and rather into a nice soft bush (or, "roll left, you'll fall 5 feet to another part of your roof, instead of 30 feet to your death). I've never had the pleasure of falling off my roof, so i'm not sure how likely it is that in my descent i can maneuver somewhere (or tumbling down my steep shingles) other than where gravity wants me to go, but i always think of an exit strategy - maybe it just makes me feel better, not sure.