I make my living on roofs, painting, roof cleaning & gutter cleaning, then Christmas Light Installations during the winter. I'll try my best to give you the safest way possible.
Make sure to have a capable ladder and get some
ladder standoffs for it, then place it to where you climb directly to the roof. Most accidents are caused in transition to & from ladders/roofs, and setting a ladder up on a gutter is a recipe for disaster. I've known painters who've had very serious accidents relying on gutters to stabilize the ladder, so I'd avoid it if I were you.
You're not climbing on the roof yet; merely positioning the ladder and climbing up it so it'll be an easy transition. If you have an extra 32' ladder, split it in half and use the half with the feet, along with a
roof hook attached to that ladder, to roll it up to the peak, then flip it over so the wheel is up and the hook straddles the peak. This plan only works if you have 16' or less from the ladder to the peak. If you have more than that, my solution would depend upon how much you want to spend and how comfortable you are at heights.
90% of Christmas Light installs are done from roofs, in the pouring rain, on high houses with steep pitches, so we've tried all the goodies. I'll give you suggestions and you can take it from there.
If you have the funds, you can invest in some
Cougar Paws, which are roofing shoes that give you traction better than any shoe can offer. If not, invest in some Merrell shoes or something similar with Vibram soles. They are the next best thing, but are still a far cry from Cougar Paws.
If your distance is more than the span of your ladder, the 2 safest choices would be to either get some
Pitch Hoppers or the
Goat steep assist.
Once you're at the peak, you'll be able to installs some
roof anchors in targeted areas. This will allow you to to have a solid system after you buy a harness, shock absorbing lanyard, rope, and rope grab. HD's in my area sell them in a 5 gal bucket like
this.
The biggest snag in this entire thing will be that unless you buy the Goat Steep Assist, there will always be the initial ascent and final descent where you aren't rigged in, which is why I suggested the ladder hooks as well as the Pitch Hoppers. Pitch Hoppers are magical little time savers, but they still come with the risk of not being properly tied into a system.
After some rough math, you'll likely notice that the initial investment, (ultimately depending upon your choices), will cost anywhere from $900-$2,k+. How many times could you pay someone to do this for you before you saw a return on your investment? Only you can answer that. I applaud your drive and willingness to learn though. I've spent the last decade learning how to safely climb 80-90' up the trees on my property to prune them and remove dangerous limbs.
Go slow, be safe, triple check everything, have someone with you, and go no higher than you're comfortable with. No shame in changing your mind halfway up. Good luck.
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