Jesse, I love all the additional detail that you have put into this!
I still think that we need to be extremely careful about making this token transferable. Because of the nature of how ERC-20 tokens work making something transferable is synonymous with making it purchasable. Yes it would be nice to be able to vouch for a would be contributor or member, but this will inevitably lead to, or at least open the possibility of, a liquidity pool being created, which can be done without our cooperation or permission by anyone who holds REP token, which will effectively mean that reputation within the organization can be purchased with money and not just time. In other words, in the world of ERC-20 tokens anything that is transferable is also purchasable.
I think this jeopardizes the value of the system as a whole because if we cannot trust that somebody's rep holdings are the result of actual contributions, then what do they really mean?
There are other ways to vouch for people, such as staking or locking your REP tokens without actually transferring them that we could explore - though that doesn't necessarily need to be a v1 requirement. Additionally, we could implement a separate mechanism for compensation as a fungible token that is fully transferable and would function more like a city coin.