So, how about this update just a day later. I'm now going to give Apple Mail a try, which means I'll be all-in on the ecosystem. Sounds like a flip-flop to me! So, I have begun that process.
First, I created folders in iCloud mail, then used the 'Copy To' function in Apple Mail on my MacBook to dump all of the mail I've saved for years in Gmail to those same folders. I even did a little cleaning up of labels (folders) while I was at it. Boy, I spent a few minutes reminiscing over some old save emails too!
Second, I just got done setting up my Gmail to forward all mail to my iCloud Mail. I'm guessing I'll just log into services and website and update my email address as I get emails. Some suggested setting up an auto-reply asking folks to update my address in their address books, but I didn't want this to go to some sites and businesses without me manually reviewing them.
I guess the biggest downfall of the process (not the result) is monitoring both mailboxes until the transition is complete, which could take day or weeks, depending on how hard I want to attack this. I'm a little OCD and can't just have 2000 unread emails sitting in my Gmail inbox!
As for Apple products, I bought a MacBook Air last year around this time. I had gotten a MacBook Pro for work, and after taking it home and using it exclusively for several months, and then deciding to fire up my personal Windows based laptop because of 'big brother', and watching it spin for THREE DAYS updating, all while not being able to use it, I swore then I'd never buy another Windows based PC again. I loooove my MacBook and MacOS.
Last bit of conversation... as for Outlook, I still just have a bad taste in my mouth from using Outlook and dealing with .pst and .ost files, and how incredibly difficult it seemed to move my data from old PCs to new ones, I just quit and went to webmail, first beginning with Hotmail, then moving on to Gmail. I'm guessing Outlook is 100% online nowadays, so maybe none of the same worries. But man, it was all I could do not to throw my computer out of the window dealing with Outlook profiles and data files.
Any more advice on the transition to iCloud mail from Gmail? Also, if something should happen, and I decide I want to return to the dark side, is there an easy way to move mail from iCloud back to Gmail? Apple Mail on my MacBook would work the same way as far as copying saved messages back to Gmail, wouldn't it (Copy To function)?
Thanks again!