abcdefg.com (hosted exchange with my ISP)

zyxwvut.com (Pop3)

Currently in Outlook for Windows I've had both of these e-mails set up, and the pop3 e-mail delivers directly to the Exchange Inbox (data file), eliminating the need for me to store any mails from the pop3 account on the pop3 server or keep a local copy of the mails.    The same applies to sending items from the pop3 account.

I've not been able to find a solution for replicating this situation on the Mac and therefore assume it's just not possible, so as a workaround I've set up two rules to deal with incoming and outgoing mail and no mail gets stored on the pop3 on the mac.

However as the pop3 is my primary e-mail account for sending e-mails it is very time consuming and annoying to keep having to manually change the sender to zyxwvut.com, in Windows Outlook this was in most cases automatic when replying from the Inbox.  I've sent about a hundred e-mails and forgotten to change the sender to the pop3 domain confusing a lot of people.

I've tried to identify 3 possible solutions below - I would like suggestions on these or possibly any other solution.

Firstly, I wonder if there is a simple solution to this and if anyone has a better suggestion for my problem above rather than using the "Rules" to achieve what I need.  Any other ways to overcome the sender problem, 3rd party apps? custom rules? workarounds?

Secondly, I was thinking that I could possibly move abcdefg.com from hosted exchange with my ISP to Microsoft 365 Online and use "connected accounts" to get the zyxwvut.com account linked on there, however I cannot find from multiple searches on this forum and others concrete evidence to suggest if Office365 connected accounts work on Mac Outlook 2011 or not.

Thirdly, I could run Outlook 2010 on Parallel Windows?  Not sure exactly how this works, but my biggest concern would be spotlight search on my e-mail which is one of the reasons I switched over to the Mac in the first place.

Thanks for all of yours time!