If someone gets access to your bitcoin wallet or whatever storage mechanism you are using fails, then that money is gone forever with no way to recover it.
If you are a regular user with no need to make a political statement with the use of a non-traditional currency, what exactly about the second scenario sounds safer?
You're arguing against cash, cash doesn't need defending.
Keep in mind that you're comparing two different markets in terms of maturity. One day, there may be a number I can call too when my bitcoin goes missing.
I'm sure people made similar arguments before e-commerce. Surely it had to seem easier to just buy a product in a physical store, with cash, with absolutely no risk of stolen credit card information on this new thing known as Internet. No issues with shipping and you can actually see the product in store. Things have changed and people are no longer as reluctant to shop online.
As interest in new areas grow, so do opportunities for business. You may not be an early adopter of Bitcoin in the way many weren't with e-commerce in the early days, but it doesn't mean it can't happen because one is easier today.
Genuinely curious--how would this work?
There may also be bounty hunters who try to recover stolen BTC on contingency, but that doesn't sound like a good business.
Why would I even need such infrastructure if I can already do that today with my bank?
Insert Mt.Gox joke here.