Rainlendar is worth a look, then, at least for fun since you bought something already -- it has a free Outlook plugin.
I had already checked out Rainlender. It's nice (and free) but the Oulook plug-in is one-directional, meaning you still have update the Outlook calendar directly. With Remind-me, you can update the Remind-Me calendar and you can synch from Outlook to RM or RM to Outlook, or to both.....not sure I explained that very well.
If you work with Outlook and "Accept" meeting invitations, then you may appreciate the value of the synching ability of RM.
I have a laptop which serves a dual role for both work and play. Since I am pretty much shackled to Outlook for planning things, I need something that talks with outlook. Otherwise RM would have little value to me.
MLO, on the otherhand, is in a different league. There are way too many many bells and whistles for my simple needs. I read the description of the Outlook plug-in and it seems that it is not up to par with the synching ability of RM, but admittadly i did not install it to test it out.