[QUOTE=metric_taper;252787]Seeing how age/sun damaged the asphalt shingles are, I would not trust the nails holding the gutter to the fascia board.

I've grabbed spikes by the head & pulled them out of the fascia in roofs that worn. Trusting a gutter held up by anything commonly used won't give you safety. Maybe it'll steady the ladder but if you need it to save your butt my guess is some part of the gutter or the fasteners will fail & literally let you down.