But when you're getting a product for free, especially email (Hotmail/Live Mail, Yahoo, AOL, Gmail, etc) you really can't expect any provider to provide comprehensive one-on-one support as it is rather pricey. So you're right to go to a paid plan somewhere.
In my experience, a common problem with support is that they lack the knowledge and capabilities to deal with certain types of support requests. At some point, some support requests need to be escalated to the product owners within the organization. Some organizations are simply not prepared for those types of support requests.
Email does seem like a service that should be recoverable, though. If you depend on it heavily enough, you should probably:
(a) Own the domain that emails are going to. (so that if Google stumbles, you can switch providers)
(b) Have full records of all accounts & aliases. (so that you can continue to receive incoming mail following any switch of providers)
(c) Backup all email regularly. (so that you don't lose all existing mail in the event of needing to switch providers)