Two Exchange accounts, one Mac one Windows, iPhone/iPad
Update in response below...
So have been thinking about this further as I start my TRO training. Looking for the most reliable/easiest to maintain system. It's OK if it's a mess on the front end as long as it works reliably on the backend.
Windows at work, Mac at home: separate accounts at each location. Open to getting a hosted Exchange account for home email to make syncing easier if needed.
Would like to have the 2 Exchange accounts sync and work reliably without having to perform any manual workarounds. They would be syncing daily.
Would like to have an IOS native app for iPhone and iPad that my single task list would live in.
Would like an IOS native app that also has a cloud/web interface, e.g. Toodledo.
I'd like to be able to run Outlook for Mac at home vs VM and Win Outlook. OK if this requires another desktop sync app on Mac, as long as it works.
If you have a better solution, PLEASE let me know!