It wouldn't bother me much although I would initially assume they were rewearing the same clothes and not clean ones each day. Over time, when they didn't stink, it would sink in.
But that said, if it's all about points 1 and 2, you don't need to spend more than 10 seconds "deciding" what to wear. Make sure all your clothes are neutral enough to go together (but are not necessarily identical) and then just pick the first things at the top of the pile. They don't all have to be identical for this to work.
You could probably work around the same-clothes-not-clean issue by doing what service techs that deal with the public do: Get a patch sewn onto the shirt with your name on it.
People's minds are conditioned to think shirts with patches on them are uniforms.
You don't even have to use your own name. Thrift stores will sometimes have uniforms for sale with name patches still on the shirt. Aside from being comfortable with the sticker price, you'd just have to be comfortable using some other guy's name patch on your shirt.
For the record, I'd be cool with a patch that says "Peter Cooper".
But that said, if it's all about points 1 and 2, you don't need to spend more than 10 seconds "deciding" what to wear. Make sure all your clothes are neutral enough to go together (but are not necessarily identical) and then just pick the first things at the top of the pile. They don't all have to be identical for this to work.