Web widget classic dev feeback

Some time ago we integrated zendesk web widget (classic) in our app, and it is some feedback and questions
1. User cannot start chat session with file attachment, is it expected?

2. In development process was used on chat:start event from docs, and have found that event fired on each page refresh which can cause problem, in my opinion it is a bug, is it?
as a result in such case it have interesting behaviours, e.g. on chat:connected fired after chat:start which seems unlogical.
3. We have found some post related to file attachment(https://support.zendesk.com/hc/en-us/articles/4408886202394) and the question is does this settings affect web widget?
looks like chat attachments limited not only by file types, but by their size to, is it possible to configured max allowed size somewhere?

In any case thank a lot