Houses are very close-Gutter/Roof Issues

Ive never come across houses being so close but we have a house where we are doing roof and gutters and on one side of the house you can nearly step from one roof to the neighbors (other than they are not at the same level). The roof pitch is 8/12. I would like to supplement insurance for something on the gutters on this elevation as I anticipate the gutter company will ask for something because of the access issues. Have any of you who have been at this for quite some time give me an idea of what additional amount per LF you feel would be appropriate? Ive posted a couple of photos. Thanks !