yes, i repeated the process this morning and everything was good. Ive used this process in the past to keep everything organized - its almost seemless and keeps everything in order (folder wise) for migration
On outlook, I keep my documents by category and year
Eg: Soccer Folder 13
Baseball Folder 13
Baseball Folder 12
I have also migrated the send folder, inbox as well but naturally i make certain they are folder moves.
So basically, create or use your gmail account, check its settings...make certain that it is a IMAP only account via the internet interface - gmail:settings (it wont work if gmail is pop3)
Then add the account to outlook, making certain it shows up as a imap not a pop3
Once gmail was created/updated, confirmed as Imap and added to outlook
I copied the folder placing it into the gmail inbox (it gets created as a sub-folder to inbox as you would expect)
leaving the original folders where they resided (backup)
I then checked the folder to confirm there existance on gmail as sub-folders on outlook (there where i noted that duplicate emails were dropped).....eg: using a rss reader or something similar I forward copies of information multiple times - duplication. once I confirmed the data integrity
Then it was just adding gmail to mac mail copying the folder over to where I desired
on my mac or in the cloud or both,
I have used this both ways mac to pc and pc to mac (in the past) and I have only retested the pc outlook to mac mail this morning
the only key issue you may encounter is email accounts (sends/receives)
Eg lets say I have a Yahoo.com or a Live.com email account on the outlook side and you are migrating all to Icloud.com or me.com only
(meaning no yahoo or live mail account set up in mac mail - you may not have that old account link to resend the email through that service)