I would concur Bruce. At least in Skagway, you're at sea level and you have an "out". If I were going to do Silverton, I'd want something like a Quest Kodiak (turboprop) that was built for mountain ops. Of course, either place could be pretty hairy if there were much wind blowing.
The problem with mountain strips is that it is not possible to establish "reliable" air service because they are usually totally unsuitable for night and/or instrument operations. When I went to Skagway for the rotary run in 2011, I considered flying in and out via Wings of Alaska, but nixed the idea when I found out that it was a VFR operation. I needed to make connections in Juneau and needed the link to be reliable. Apparently WOA has minimums of like 500-1, or something like that, which is pretty low. I am pretty comfortable flying in MVFR, but where I come from, 500-1 is considered Low IFR, and I'm looking for an ILS or LPV approach. Things are different in Alaska!
/Kevin