@Brady I made the same decision some time ago and then truly regretted it :)
I ended up with a plugin that registers Events CPT, adds a metabox /w datepicker, changes the request filter to order events by their date and hide the past events. There is also an ajax driven front-end calendar of events. It's far from perfect but let me know if you will decide to go this way and I will put it on github or somewhere.