I'm going to third the coolidor suggestion. It can be used to store most cigars, especially boxes, tucked away pretty much anywhere. Then, a nice, smaller humidor can hold more immediate smokes.
Anyhow, I think a desktop humidor is a good idea, just don't be surprised how quickly that coolidor is needed.
As for the actual cigars, try a bunch from different countries, with different wrappers, etc. and you'll start to figure out what you like.
Oh and welcome from Western Oregon.
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