Welcome to OB and to the addiction, lunarlemon! I'm an erstwhile Ashevillain myself and still missing the mountains. Maybe someday we'll get back...
Definitely check out the Western NC Orchid Society, the group putting on the orchid show in April. This year's will be an extra-big fete but even in a normal year they put on one of the better orchid shows in the eastern US. The group is also very active and friendly, and by going to monthly meetings you'll see, learn how to grow, and have opportunity to acquire a huge variety of plants. Forums like this are great but no substitute for hands- and eyes-on cultural advice from experienced growers.
As for what'll be easiest for you to grow, that's a tough call since it depends on so many variables, chiefly your personal plant-tending habits and aesthetic preferences. For me, what's 'easy' arises from some combination of what suits my growing conditions and what I like and will pay attention to. I like Dennis (Orchid Whisperer)'s advice to get really good at growing what you already have, and John (Subrosa)'s advice to find plants you can grow outdoors year-round.
re: Draculas, in my limited experience (I've killed 2 or 3) they're very intolerant of cultural inconsistencies and are among the more challenging Pleurothallids to keep alive. Very pure water is important for most cloud-forest species, and if you really want to grow these well you'll probably need to water them with RO or distilled rather than dechlorinated tap. Seek out Andy's Orchids at the upcoming orchid show, they sell a vast array of Pleurothallids and other groups and can give you both solid culture advice as well as the hook-up on a lot of cool plants you won't find elsewhere.
All prior rambling aside, two of my favorite relatively easygoing orchids are Dendrobium kingianum and Paphiopedilum delenatii. Both are compact to varying degrees (I've seen kingianum clones from 2-14+" tall though most are in the 6-10" range), beautiful to look at in and out of bloom, usually very pleasantly fragrant, easily adaptable to windowsill culture, highly temperature-tolerant, and best of all common and cheaply acquired, making them a lot lower-pressure than many orchids.
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