WOW - what a list.
Before I answer any - it depends on how well you understand your orchids. If you don't feel you understand their needs, work on that first. The first year I tried growing outdoors, I had MAJOR problems with bugs and mold and moisture control. If you know what your plants need, it is sort of like growing inside, but with more pests and less control.
1 You can grow anything that your temps allow. It will vary through the seasons.
2. Mine are hanging it trees and large bushes and in racks. Depending on the species, they are in varying exposures to light.
3. I hang almost everything in wooden baskets. Fewer pest get to them. Metal racks are good for same reason. Wood seems to allow more snails access.
4. Media and watering varies to give the orchid the rate of drying it needs. It depends on the type of orchid, the amount of rain in your area (and how exposed they are), the rate of drying (humidity and airflow), and the metabolism (temperature and light). You are less in control outdoors, and have to adjust to what nature is doing.
5. I never bring mine in unless temps below 40 are expected. At 40 I cover overnight with tarps. If 35 is predicted I would add a few light bulbs under the tarps to provide a little heat. NEVER give them sudden drastic changes, always let them acclimate.
6. Read EVERYTHING in the outdoor gardening forum.
Bonus question - It can be bumpy, but I love it. Here's a link to pictures from last year outdoors. I'm getting some blooms now and will update as time permits.
Growing in trees and bushes before the new racking was complete (they were getting "bowed" from the weight:
My Old Growing area - Orchid Board Galleries
The new overhead racking:
New Garden Racking - Orchid Board Galleries