I’ve thought about a roller on a really long stick. I would just suck it up and do it if I could figure out a safe way to do the back side.
The small ladder I have is adjiustable.
It’s a 13’ gorilla ladder that could be adjusted on each side.
ex. 6’ A-frame or 13’ normal ladder
That would be able to fix the slope problem.
But, it needs something as a base.
Using a much longer version would go up and over the spine and basically give you a nice ladder to get up and down.
Buy me this and i’ll do it for “free”
http://www.homedepot.com/Building-Materials-Ladders-Multi-Position/h_d1/N-5yc1vZ1xr5Zasew/R-100430056/h_d2/ProductDisplay?langId=-1&storeId=10051&catalogId=10053
That pitch, if it’s like mine is one that you “could” walk on, but you need grippy shoes and a warm day. (I almost fell off mine when it was 45 degrees… That was fun.)
edit: this might work too.
^Wow, that can’t be a real suggestion. That is almost as good as this idea…
Goodluck Fry. I don’t think you will be able to get to that “tough” spot very easily.
Maybe call around and see if a contractor has a cherry picker and can do that type of work or knows someone.
This is why I prefer Hip-roof style homes. A-frames are nice to look at but damn it is scary shit sometimes.
Doesn’t look to bad to do. I would figure a roller with a long handle would be fine, just get up on a latter and start painting.
Oh…or just make the damn wife to it! You finish the smoker and have a cook out with your friends, drink beer and watch your wife paint the chimney!
What par of the city are you in or around?
this has me dyin…
fry, just paintball it.
Does it have to be a baby, Or can I use pets?
PM ieatpaint?
So he can eat my chimney? 
He’s given lots of great advice in any thread with questions about house painting. I’m guessing he can probably recommend someone better equipped to do the job right than the people posting, “I’ll give it a shot” here. 
i was on my roof and its some scarrry stuff when the pitch of the roof is greater then the traction you have with your feet = dangerous lol. rent a lift.
Exactly how many times have you fallen?
Maybe you should get the whole outside of the house painted…
Then get them to do the chimney for free?
Woah. Less is more.
get a midget to do it. if it falls, who cares?
He will not be hurt as badly either.
F=M*A
We could just toss the little guy up there.
find a bunch and they can stand on each others shoulders
I have nothing to contribute to this thread besides that I hate Capes, Expanded Capes and Dormers. I almost fell off my roof this past summer from sliding on the shingles. Rent a bucket truck.
I’m actually crying from laughing so hard at the comments.
get a paint sprayer and get one of those hose nozzles that has a Jet function.