But it's not clear where the idea came from. Some say that it was his mentor Roger Thomas Clark aka Variety Jones aka Cimon. Some say that it was DEA agent Carl Force aka Nob. In any case, it's clear that Ross was initially shocked by the idea.
No, the opposite is true. As the appeals decision points out multiple times, Ulbricht was startlingly casual both about hte decision to order people killed and in his reaction to evidence that the killings had occurred. His ostensible hired assassin informed Ulbricht that he could have a target killed, but that he couldn't attmept to recover Ulbricht's funds unless he also paid for the assassination of several of the target's associates --- people Ulbricht had no ostensible connection to at all. Ulbricht essentially said "fuck it, whatever you think will help recover some of my funds" and paid for additional gratuitous killings.
Importantly: this case had apparently nothing at all to do with Force, who was involved in a different murder-for-hire scheme, one for which Ulbricht could still stand trial (but probably won't, since his life sentence is now overwhelmingly likely to stand).
We don't know. The prosecution's burden was to prove beyond a reasonable doubt, to a jury, that Ulbricht himself believed he was ordering people killed. They succeeded, and it's not hard to see why.
I don't disagree that he was ordering people killed. Even if it was all shadow play, driven by scammers and LEA entrapment, it was a moral failure.
In hindsight, the better option would have been adequate security, to prevent interference by adversaries. Also, there should have been policy and mechanisms in place for dealing with adversaries.
Silk Road clearly demonstrated a broad unmet demand for drugs from trusted sources. With trust based on user ratings. And by philosophy and necessity, it operated outside mundane society. If there were no laws against drug use, he could have just sued people or filed criminal charges. In future, the second realm will need its own enforcement services. And insurance.
The chat logs of the first incident seem to suggest that he took some time to come around to it but he didn't seem to find it particularly horrifying or objectionable.
The burden of proof is on the government to prove that those were his chat logs and they weren't altered. Until he's formally tried he's innocent of that accusation.