I had the same dilemma as I used to be pretty much reliant on the MS ecosystem (& used a Windows Phone). I never liked the idea of the Outlook app as it caches your userid & password on some remote server, just waiting for a schoolboy to hack it.
I was hesitant at first but I exported my Windows Live calendar & contacts to Google. I now use Google calendar on both my laptop & phone & have not looked back - I think Google calendar has a slight edge.
Might be worth a try for you as this option leaves your Windows Live calendar intact (save for any new entries you make post export) so you can always revert if you don't like it. Exporting/importing is an absolute breeze, so you don't have much to lose.