Glad to hear your considering HelpSpot!
Yes, customers getting a new request do receive a notification email. This email is generic and gives the customer their request ID, a link to check their request online as well as links to the other portal resources (you can customize all emails).
The system doesn’t send out an email under normal circumstances when a request is assigned. I like the idea of this though and will note it for consideration in a future version. The big downside I could see is that sometimes you may not want that email to go out, so the feature would need to be done in such a way that you could control that.
Yes, you can auto assign requests. When you setup your categories you must assign a default staff member. Optionally you can also tell HelpSpot to automatically assign any new requests in the system for that category to the default staffer. By doing so any request where the customer selected “how to” from the drop down would be auto assigned. Note that you must also mark that you want the category to be publicly available. When you do that it will automatically appear in the portal.
Another feature which may interest you is that you can do the same thing with email accounts. So if you setup a firstname.lastname@example.org account you can tell HelpSpot to check that account and any emails it finds there will be automatically placed in the “how to” category and assigned to that categories default staffer.
Now there may be a way we can accomplish putting these together. All the email auto responses support “placeholders”. Currently there are no placeholders which will dynamically place the assigned staffers information into the email, however, that is very easy to add. It also happens to be on our list for an upcoming release. So while you can’t do that today, it will be in HelpSpot in the near future.
Hope this helps. Please let me know if this somewhat long winded explanation needs any clarification.