I actually tried switching to MobileMe
Towards the end of the longest free trial in MobileMe history, I found myself quite enjoying seamless syncing of my contacts, calendars, keychains, and Safari bookmarks between my 3 Macs. Having access to iDisk was nice as well, although I found it to be a bit slow to synchronize at times. I didn't like the MobileMe photo sharing features, and ultimately decided on paying for Flickr. So, I was looking at paying $100/year just for syncing and iDisk.
I have been paying $50/year for IMAP e-mail over at pobox.com, which I have generally been happy with. So, I figured that if I took that $50/year charge for e-mail and folded it into MobileMe, then paying $100/year to Apple would be justified.
So, I switched my e-mail to MobileMe, by adjusting my forwarding addresses to route the e-mail to MobileMe.
And let's just say that it didn't go well. There were two main problems. The first is that for one of my e-mail addresses, mails were either delivered incredibly slowly, or not at all. Several of my friends complained of getting their e-mails to me bounced back at them. I didn't really investigate this too much (because I didn't think that too many people were using this address), but it seemed to be some issue with how MobileMe accepted e-mails from the UNIX host that managed my secondary e-mail address.
The biggest problem with MobileMe mail, however, is that you cannot change your from address when sending through Apple's servers. This means that if you want to use MobileMe as your primary e-mail, everyone will see "yourname@me.com" as your return address for every e-mail that you send. And then in the future, when you decide you want to switch off of MobileMe, you'll have to notify all of your contacts to update their address books, which is stupid and annoying. This is why I use a forwarding e-mail address -- so I'm free to change my mail backend at will, without having to bug all of my friends to use a different address.
So, I cancelled my MobileMe trial (just days before I would have had to start paying), and left the following feedback for Apple:
"Hello,I am evaluating the MobileMe service, and have recently begun an attempt to use it as my primary e-mail system. I use my "ajr9@po.cwru.edu" e-mail address as a forwarding service, and have configured this to forward to "areitz@me.com". This works well, and I am able to get new e-mails on MobileMe (the performance over IMAP is actually quite impressive, to boot). However, I would like to configure my "from" address to be "ajr9@po.cwru.edu", so that when I send mail, my contacts see that it came from my forwarding address.
When I attempted to configure my MobileMe account with my custom "from" address in Apple Mail (v3.5, 929.4/929.2), I get an error from Apple's MobileMe SMTP server, that indicates that this configuration is not allowed. I have confirmed with MobileMe support that Apple doesn't support a "from" address of anything other than "@me.com". I find this to be unacceptable, because I don't wish to change my e-mail address, and I don't want me contacts to become confused, when they see e-mail from me that comes from a strange address.
I would also like to note that Google's Gmail and Pobox.com's Mailstore service both allow a custom "from" address to be used with their SMTP servers. So, it seems like adding this feature would help MobileMe maintain parity with the commercial e-mail world.
While I have enjoyed the syncing and iDisk capabilities of MobileMe during the free trial, the inability to send e-mail with an arbitrary "from" address renders MobileMe e-mail unusable for me. And unfortunately, without the e-mail component, I don't think that it is worth $100/year just for address book sync and iDisk. Thus, I will be cancelling my MobileMe account.
I would be interested in becoming a paying subscriber, however, if you offer this feature in the future.
Sincerely,
-Andy Reitz."
And with that letter, I switched (somewhat reluctantly) switched to Gmail. Even though I'm a little wary of doing all of my e-mail through Google, at least Google allows me to respond with my forwarding e-mail address, and doesn't bounce mail from my friends (that I know of).
-Andy.