A lot could be done to make voting simpler. If voting is important, then a relative amount of effort is needed to make that obvious.
I'm not clear if my holding gets shared equal weighting between those I vote for. If I only vote for 1, do they get full effect or no difference from if I had voted for 2?
Having an alert to the effect that this will transfer the account balance, is not what user will expect. Someone wanting to vote, is not expecting to transfer their balance somewhere.. transferring it to the same account does not make sense. Also, it's hard to keep in mind which 101 delegates you prefer. Perhaps just encourage people to an optimal number of 10 or more.
Off topic perhaps but I do not understand how we know that 101 delegates is sufficient to provide a robust network. Are we expecting more delegates in future? In the event BitShares goes large, what is to prevent a simple DDOS attack on the core delegates??