I would not lean a ladder against the balcony railing. It may not support the weight of the ladder and a human. 
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This decision is a very personal one for the inspector. I personally would not walk that roof. However, I would attempt to get to the high side of the chimney. Chimney’s can be weak points for water intrusion. I like to put my hands on the shingle somewhere if possible so I can closely evaluate the condition. The remaining planes of the roof could be scanned with a good set of binoculars.
I use a couple of safety features with my ladders. I have leveling systems. I have stand-off bars. If I am at roof edge, I use a bungie to tie off to the gutters. You know our SOP, so combo it with other tools and techniques.
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So, My doble ladder technique worked a charm. My heavier sturdier ladder for the primary climb, and having my lightweight aluminum extension was perfect as a secondary ladder that was easy to lift up and place. I did not have to lean the ladder on the railing either, I could not see it in the photos but once up close and personal I realised the railing was set back so I just had to lean the ladder up against the roof structure.
Huzzah!
Oh, and Brian, I would not blame you for not walking that roof. Its pretty tall. Thankfully the shingles were nice and grippy, none of the loose granules you sometimes find, and maybe its because I used to do a lot of rock climbing, or maybe im just dumb/brave, but I felt comfortable up there, just spider crawled/butt scooted my way across. No way was I going to be standing up and walking up there.
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Maybe with these, they are pretty awesome.
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Fair point, but you cant trip or stumble if you are butt scooting! 
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That would depend on how clumsy one was, eh? 
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Get a good drone and become familiar with how to use it efficiently. Good drones have unbelievable cameras. You can get as close as you need to roof penetrations and other items of interest. And while you have the drone up, you can take a nice aerial view of the home/property to really impress your clients!
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Bert, I’ve used that method many times when needed. And, have had no ill effects.
Plus, it looks like the chimney needs some attention.
BUT, stay safe first and foremost!
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Worst part of mounting a roof for me is getting back on the ladder to come down again. I bought these extension rails and it changed my world for the better. [https://www.homedepot.com/p/Guardian-Fall-Protection-Safe-T-Ladder-Extension-System-10800/203191566] 
You step between them to get on and off the ladder.
With these and a Werner triple 9’ extension ladder I can mount most 2 story roofs that are safe to walk.
Be smart, be safe. 
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One caution on the flat rubber roofs, like is probably on the balcony. The rubber membrane can get brittle after about 10-15 years. You start walking on that roof, that hasn’t been walked on since it was installed, and you could damage it…just by walking on it. Now you are liable for a new roof and any water damage inside. I was accused of walking on the flat roof and causing damage/leaks inside, but I told them I didn’t walk on that roof for that exact reason. Turns out the cable installer did, and the cable company then had to pay for all the damage and repairs. So be careful on the rubber roofs.
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I’ve done that before… climb onto one level and then lift the ladder up so I could get to the next level. Just have to use best judgment that it can be done without damaging the structure. And just keep in mind you are that much higher off the ground, so be sure you use discretion and/or caution on the roof. It’s quite a drop.
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George, that is a great thing to keep in mind. I noticed these roofs did have surface cracking, but thankfully they were nice and sturdy. I always make sure to test the roof with my hand, as well as with some light test steps prior to going for it, but of course that wont be 100% effective, or apply to the entire roof surface. I will still be working towards that camera, and possibly a drone down the line. My understanding is that drones come with their own host of potential liability issues.
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I personally would not get on that one. I do get on two story roofs whenever I can, but not if I have to climb the ladder all the way to the second story from ground level. One mistake and you could be done for a year… or worse…
That’s why I always have a drone with me. I have the mavic air, which is great, but the Mavic Mini is only $500, and takes amazing photos if you want to go cheaper. You also dont need the license for that one, its 1 ounce below regulation.
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Technically you do need a license since it’s commercial use. Technically.
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And, if one adds prop guards, it is over weight.
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This thing with a GoPro works awesome. I just did four 3-story apartment complexes with this thing. Ironically, I used a shorter version at the Venetian in February. Used it on all of the gondola bridges, and the front pool.
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I have used a drone on multi-story buildings, If your not proficient with a drone I dont recommend, its a costly investment that could be lost.
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Yes you do need a license( Part 107) for commercial use, your putting yourself and your client at risk for fines if not licensed and insured.
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The civil penalties for flying a commercial rig without first obtaining a remote pilot’s certificate from the FAA are up to $32,666 for each incidence.
This fine is charged per day for continual illegal use of a drone for commercial purposes, after receiving a warning letter from the FAA.
The FAA may also impose criminal sanctions, which include a fine of up to $250,000 and/or a prison sentence of up to three years upon conviction.
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Welcome to our forum, Larry!..Enjoy! 
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