The thing about late Aug is that is when the salmon are in and that means more chances to see bears in Ketch, less so Juneau and many other cities. If in 2024 better get moving as hotels, flights and shore excursions are likely to be fulling up.
Since the dog camp is at a specific spot sometimes they can't fly there but can fly to other spots on the glacier or nearby glacier. Be ready to answer the question "Do you still want to fly to glacier without the dogs". That should also come with slight refund. Not sure how it works with ship line sponsored excursion. May want to check with shore excursions.
Is it her airfare and her excursions or excursions for both. Better get firm decisions on excursions as they are so expensive in AK. Excursions very easily could be more expensive than the cruise.
June is too early for salmon (like you said) which makes it to early for bears at the streams. In ISP I would think about switching to whale watch to see whales and the possibly of bears on the beaches. Photo below from whale watch several years ago June 27/2014. fyi my favorite Juneau/ISP webcam. TheSnowCloud Juneau area Webcams. I forgot to answer your question Skip Mendenhall by bus.
What time of year? May recommend changes based on time of year.
In Juneau do whale watch. All whale watching is different and Juneau will be spectacular. If you want to visit glacier do it via helo. Not cheap, weather cancels sometimes but you will never forget the trip.
I think your main problem is October. All the bears likely gone, the weather sketchy and much of the park closed. It is a quick flight but ferry is not fast enough even if there were one.
I thought that Wrangel was a great place to see black bears and it seems that this would be a good time of the year. Not from personal experience but just what I remember reading.
Look on youtube for last years Alaska hikes. Skagway has great looking ones easy and hard. Some train up hike down. Look for personal ones. Chris Wong is one name to search Ak cities.
Except for the ginger buy it in ANC so you don't have to pack it and worry about customs. You can also get what you have forgotten. Lots of stores. If that short of time you may have to rethink your visit.
We had good luck with Costal Helo in Juneau. Call direct. Remember AK time is one hour later than Seattle. Many times weather cancels so be ready with back up plans. Likely been full for several weeks but may have someone canceled. Skagway may have better chance with better weather.
I think that most of the rental cars have to be picked up at the airport this year. Not 100% sure but something to check and factor in getting to and from.