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What works for me is contacts in Gmail as is synchronise with all Android devices - combine that with emClient using IMAP on your PC which also pulls in your Contacts, Calendar, Mail and tasks and add your other accounts with POP then I think this will work well.
The free version of emClient let you use two e-mail addresses - it may be worth a trial run. It also imports your stuff from Outlook. Importing contacts from Windows Live Mail is sometimes not working.
Outlook does not play well with Gmail.
Depending on your functionality needs, Trello is an incredibly flexible platform (I use it as a no-frills CRM system). It has the advantage of being free and cloud-based, but if you need to integrate other applications (e.g. chrismine's description of emClient) then it probably won't be a good fit.
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