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The rolled leaf is likely a caterpillar issue.

https://www.gardeningknowhow.com/ornamental/bulbs/canna/managing-canna-lily-pests.htm

As for the cannas- They are tropical, and would be best brought in for the winter. You can dig the bulb up, and store in a temperate dark area until spring. Here is a link that will help: https://www.gardeningknowhow.com/ornamental/bulbs/canna/storing-canna-bulbs.htm

As for the corkscrew grass. They are hardy perennials in most climates. Here is a link on their care as well: https://www.gardeningknowhow.com/ornamental/foliage/corkscrew-rush/growing-corkscrew-rush.htm

Personally I would wait until they dry, but it would survive cutting now. Here is an article that will give you more information on wintering cannas:

https://www.gardeningknowhow.com/ornamental/bulbs/canna/storing-canna-bulbs.htm

Yes, plant canna bulbs in spring after the last frost date in your area. Even with established plants, they will be able to establish more strongly if planted in spring. Since you are likely in zone 7 or 8, cannas are winter hardy in your region, so you won't need to dig the bulbs up in the fall.

https://www.gardeningknowhow.com/ornamental/bulbs/canna/canna-lily-care.htm

I believe this to be a fungal issue. I have a method that I use to cure, and prevent further disease. It is alright if you don't have every ingredient, but the soil priming you should not skip. the recipe is as follows:

First, you will want to prime the soil with dolomitic lime, then spread wettable sulfur to Kill off any infection in the soil. I Also like to spray the plant itself. Mix a few drops of one or more of these ingredients into warm water with a spoonful of coconut oil: Rosemary oil, lavender oil, neem oil, garlic oil, cinnamon extract/oil and for really bad cases, also add clove oil.

Here is an article with more information on the plants:https://www.gardeningknowhow.com/ornamental/bulbs/canna/canna-lily-care.htm

They could be too young to flower, or you may need to give them some all-purpose fertilizer to help them out some. Here is a link to some articles for more information:

https://www.gardeningknowhow.com/ornamental/bulbs/canna/