Probably not what you are looking for (I used to use Kies to Sync to MS Outlook 2007/2003).
But Microsoft ditched the Outlook. com app to Microsoft Office Preview which gives an "Outlook" app rather than the Outlook. com app which only displayed email. They updated Office preview again in the last few days (this maybe the issue) and will probably call it the Outlook app.
I have my Outlook Calendar in S-Planner, you can un-select other Calendars.
You can put the Outlook. com web calendar on pc, it's very good, and an entry instantly appears on the S-Planner and Outlook app. Whether it retains old entries I would guess so in Settings.
You can use a live.com address, use an Outlook.com address or change live to Outlook.. It will support Hotmail if you agree to change your address to Outlook.
I don't know much about this really, but I like it a lot, and with One Note and One Drive etc it works nicely for me. I wanted to be able to stay offline and store locally, but I am warming to this as a better alternative to Google, though you lose more seamless integration with everything using Google and Google now, and I am warming to that too. I don't really use my Gmail account for anything personal though.
I hope this helps if you are not stuck on Exchange, which I never used.