Five years seems like a long ass time if you consider Bitcoin has only been around for six and SR only existed for around 3-4 years. So I have been thinking about what will happen to TOR and the Darknet down the road in 2-5 years? Will it still exists like it does today, centralized market with everyone's coins being held by a central authority? Or will we shift to multi-sig only markets after a few more scams, seizures and hacks? Will I2P flourish? Or will it just die out as another Darknet solution? Will things like Syscoin and OpenBazaar be relevant at all? Please share your opinions, speculations and Bailey Jay poems.
The Grand Wizard expects to see a shift toward p2p/decentralized marketplaces as soon as user-friendly apps are available. Any p2p market will have to implement multisig and so we've been encouraging customers to try 2-of-3 for themselves and get comfortable with it. Multisig definitely has a learning curve but once you've done a few transactions you'll find it really is not a lot more difficult than GPG.
Of the three candidates the Grand Wizard has seen Bitbay is presently envisioning a decentralized but moderated marketplace which will remove illegal listings. That means they will be useless for our purposes. It also means Bitbay is doomed to failure: it meets no need which isn't already being adequately served by eBay, Craigslist and other large centralized marketplaces.
Shadow Market requires that users adopt not only new software but also a new cybercurrency. Given the lengthy history of scams in the cybercurrency world that's a pretty big hurdle. And while Shadowcoin brags about all its super privacy features, at present the simple act of buying it draws attention. (At this point chances are good that anyone buying Shadowcoin is looking to use it for nefarious purposes and the market cap is miniscule next to Bitcoin's).
Edit: The Grand Wizard has learned that Shadow Market plans to offer an open community Shadowcoin/Bitcoin exchange. This would take care of many of the objections I listed if they are able to implement it. (The Grand Wizard thinks this is a pretty big "if," and notes that it would require having a sizable pot of bitcoins sitting in a hot wallet -- something which has historically proven irresistible to hackers and which could lead to many of the problems we already see with centralized escrow).
OpenBazaar is probably the most promising of the three. Unfortunately, the latest iteration of OpenBazaar relies on UDP and so can't be used on Tor. This is not necessarily a deal-breaker as it can run on i2p, but again that requires adopters to not only learn OpenBazaar but also master another clunky and complicated system. (And given how badly the Shit Road Regurgitated admin has blackened the name of i2p with his constant Reddit shilling, it's possible nobody will ever take eepsites seriously again).