Syncing offline Outlook 2011 data to icloud and google

Hello,

I am running OSX 10.9.5 on a 2011 MBA (4gb ram). I have Outlook 2011, v14.4.8 installed. I also have an iPhone 5 and an iPad that I use.

EXISTING SET UP

I used to have an exchange account from my former employer.

I set Outlook to "work offline" upon my departure and continued to add contacts and calendar entries to this account. However, no email traffic in Outlook.

Have backed up this file as .olm archive

I use gmail (web based, app on iPhone) as my primary email.

I have deleted all prior data in iCloud Calendar

DESIRED SET UP

I would like to be able to:

- Add gmail to Outlook (DONE, though still offline)

- Sync Contacts and Calendar from Outlook -> iCloud and Outlook -> Google so that all 3 systems are connected on MBA as well as iThings

PROBLEMS

1) Calendar

- Unable to import .olm data into iCloud (exported calendar, converted to .ics file using OLM Converter, imported to iCal, however only certain entries importing)

- Unable to import this .ics file to google calendar.

Question:

- How do I get calendar data from offline exchange account to iCloud?

- And how to I get this data to sync with Google?

2) Contacts

- Unable to cleanly import tab-delimited csv file to Excel for import into Address Book/ Contacts

Question:

- What is the best way to bring contacts data from offline exchange account into Contacts?

- And how to I get this data to sync with Google?

Many thanks,