Well I'll have to thoroughly test it and see if it is a solution for me. I'd be curious to hear your thoughts on the questions I posed regarding compatibility.
For those wondering, I did successfully set up my iPad 2 iOS 7.1 with my existing settings using iCloud as the conduit for my variety of e-mail addresses. I'm happy to report it worked just as it always has. There were a few frustrating moments, but they were due to entering settings incorrectly. Once I got that corrected everything is humming along.
I didn't want to get into a full test of how well Outlook.com Exchange integrates with iOS and OSX, but I briefly set up my Hotmail account using the Outlook.com option. It was pretty straight forward. I didn't have any mail in the account to play with because it all gets forwarded to iCloud and I just didn't want to get to far into it. I didn't notice any issues with folders having different names, but I did not see an Archive folder. Maybe because I hadn't technically archived anything yet for that new account?. When I tried to move an iCloud e-mail from another iCloud based account to my Hotmail Exchange Inbox to play with, it wouldn't allow me to on my iPad. Looks like you can't transfer mail between different account's folders with that setup. At least not from iCloud to Outlook.com. Even with IMAP I could do that. I sometimes do transfer mail from one account's inbox to another if I inadvertently give out the incorrect e-mail to someone, or they don't have my most recent one. That way I can keep all my pertinent emails organized under the account I want them in.
I like the sound of this Exchange thing though. And the fact that I've never actually given out an Apple e-mail address to anyone, or cared to, I'm not married to iCloud, just the functionality. I also don't ever really use webmail, but it'd be nice to have that work on Outlook.com. I can't send from my domains on iCloud.com. I'd honestly prefer a more straight forward approach to all this, but I've gotten fairly good at setting this up and the iCloud method works well for me now. When my e-mail hosting account is close to renewal time, I may consider taking the time to really investigate a switch.
If anyone has been doing this iCloud workaround and then moved their domains over to Outlook.com's Exchange solution, I'd love to hear about your experience.
steveschklar - This Outlook.com Exchange thing sound like a much simpler solution for you. If I were setting something new up I'd look into that first. There are a bunch of tutorials out there. Basically you just need to set up your e-mail domains with www.domains.live.com (Outlook.com), change the MX records for your domain with your host, and then setup those new hosted accounts on your Apple devices. (Back up all your mail to be safe.) It appears the latest version of Daylight's DMA (4.1) supports Exchange. Actually if I were still in admin work, I'd be totally interested in that product. Looks cool.