Outlook in parallels

I didn't see a forum where this question is a perfect fit so forgive me if this is not a good spot to ask for help.  I am wanting to make the final plunge and get rid of my last Windows unit.  My last hang up is CRM, I am a small business and have relied on, and been happy with Outlook for at least the last 15 years.  I does exactly what I need -- the problem I am (think) I am having is that if I use (which I already have on my MBpro) Outlook for Mac it won't sync between Outlook and iCal, Cantacts, Notes, Tasks, Etc.  Currently I use iCloud sync for Windows and it's great, everything works correctly-syncs and my MBP, iPhone and iPad all have the same info.  Is there any reason that I couldn't install Windows Outlook in Parallels, use the same iCloud Windows Sync and not get my same end result? 
I am open to other ideas, don't care about Outlook's email, but the contact options and the ability to make Contact Journal entries and see past activity with a contact is what I can't seem to replicate in Mac World.  It doesn't seem like a big deal, but I can't find it and I don't want to pay $99/mo for a CRM that will take me to the moon when I only need to get to the corner.  I will make a journal entry with meeting notes save it in outlook, and then just to be save and prepare for an eventual change I print the note as a .pdf and save to that client's folder.
Any and all guidance appreciated. Thanks.

Don't think that's possible as iOS devices can only be synced to one iTunes library at a time.
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