Help syncing new iPad with Outlook 2007 on my PC and Blackberry Tour 9630

I have searched for answers and am stumped and frustrated...
I bought an iPad (am trying to become I-friendly) and thought it would be convenient to be able to sync my “stuff” (Contacts, Calendar and notes) to the iPad so we’ll have access to it while traveling.  I use a Blackberry Tour 9630 and a PC with Outlook 2007.  I have synced them effortlessly for years using Desktop manager.  I make changes to my ‘stuff’ on both phone and PC and when I sync - the most current ‘stuff’ gets placed on both.  Voila!  Not anymore.
When I set up my iPad to work with iCloud things got screwy.  A LOT of my contacts just disappeared - mainly the ones I use frequently.  Now my Outlook 2007 calendar has three calendars on the screen:
Calendar in iCloud - pink
Calendar Merge Conflicts in iCloud - green in a tab behind the pink calendar
Calendar - blue
I use a cox email account and my blackberry gives me the choice when deleting an email whether to delete on the device or on the server.  I use that feature a lot when we are traveling for a few weeks.  It is nice to come home with no redundant emails on my PC.
1-How do I combine all the calendars so I have the same thing on each device, Hoping to stay updated on each when I make changes
2-Can the iPad email give me the option to delete from the server when viewing an email on a cox.net account?
I am not an expert but fairly tech savvy and usually can get these things done. I need help!  I appreciate any thoughts or suggestions - Thanks in advance

Make sure all content is transferred and device is backed up before you update.
Transfer purchases
http://support.apple.com/kb/HT1848
How to backup
http://support.apple.com/kb/HT1766

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