If you will allow me to play devils advocate. I have very little faith in the mental faculties of my fellow man. Consequently I find it hard to believe that dash failed to gain traction on the darknet markets it was introduced on as a result of any sort of technical understanding on the part of market actors. Meaning, to most of them, monero is going to appear indistinguishable. What reason do we have to believe a private currency will gain traction this time when it failed last time?
My understanding is that both Oasis and AlphaBay implemented Monero on the basis of demand, rather than speculation or compensation by the currency team. It is possible that this is just PR and they are doing it on speculation, and already found sufficient profit by front-running the public information. We will discover that soon enough, by observing listings and transaction volumes.
The lack of multisig is definitely hurting now. Probably more so than lack of GUI. A Tor-accessible web wallet with multisig support would be basically as good as a GUI for usability. In fact it would put us way ahead of Bitcoin in terms of usability.