iCal Export / Import to Google Calendar Fails

Regarding the maximum .ics (iCal) file size: I today (August 2017) successfully imported a 4.5MB file into our Google calendar. An attempt to import 10MB and 8.5MB .ics files failed with the error (if memory serves) : "Failed to import events: Unable to process your iCal/CSV file." If you know the structure of the .ics file you can edit it down to size (carefully) using a text editor. This page currently details the structure: Import events to Google Calendar - Calendar Help . Also, consider exporting, then deleting old entries as there seems to be an undocumented space limitation resulting in a message implying a user has exceeded the event entry limit. Unfortunately the ability to delete a date range of event entries (like a month) is either not currently supported or is hidden (click then shift-click did not select a range when I tried it in Firefox).

I had no problem importing my iCalendar file, I'm using Lion too.

Google's help page on the subject is as follows:

If you're having trouble importing iCalendar files into your Google Calendar, please check the following formatting tips to make sure that your file is formatted correctly:

• Are your headers and footers formatted correctly?
  All of your events must be entered with the correct headers and footers. If your headers and footers are not formatted correctly, or if any of your events are not entered between a header and footer, you will not be able to import the file into Google Calendar. For more information on iCalendar files and field headers and footers, please click here.
• Is your file too large?
  The recommended file size when importing files into Google Calendar is 1MB or less. If your file is larger than 1MB, try importing events from a smaller range of time. Most calendar programs offer an option to limit the range of time during the calendar exporting process. If your calendar program does not offer this option, you may need to manually edit the iCalendar file to divide it into two or three smaller files. When doing so, please make sure that you copy the correct field headers and footers in each file.
• Are you getting a “Processed 0 events” error message?
  This error often occurs when you may have clicked on the “Import” button more than once. In this case, your events were imported with the first click, but no events were processed with your second click. Please try searching for one of the events that should have been imported and if you are able to find it, your import was successful. If you are unable to find any of your imported events, please try importing the file again. If your problem still persists, please create a new secondary calendar and try importing the file into the newly created secondary calendar.

You should get the same results by syncing your google calendar with your iCal through CalDAV support...

http://support.google.com/calendar/bin/answer.py?hl=en&answer=99358#ical

Hope this helps!

All this advice would seem to make sense, but I'm having the following problem:

1. In trying to import a calendar from iCal to Gcal, Gmail will allow me to select only one file at a time. My .ics files are each individual events, not entire calendars. So EXTREMELY cumbersome to copy each one individually. Are the files that you all are talking about individual events, or have you somehow condensed an entire calendar into a single .ics file?

2. Additionally, even once you've imported a from iCal to Gcal, is there any way to automatically sync them, so that adding an event to iCal automatically adds it to gmail? It works in the other direction, from Gmail to iCal. If not, does that mean you have to manually reimport the calendar each time another few events are added to your iCal? How nonsensical!

3. And finally, the only reason I want to shift everything over from iCal to Gcal is the following: I prefer iCal and find it more user-friendly, but some of my events get scheduled on Gcal through shared calendars with other google users. So I've synced my gmail to import calendars into my iCal. No problem. EXCEPT, when I want to share my entire schedule with someone from iCal, only the iCal-original calendars will share; there seems to be no way to share calendars imported from Gmail. So I tried working in the other direction, knowing how easy it is to share calendars in gmail - but now I can't efficiently sync my iCal calendars into Gcal. How infuriating! Is there no way to streamline this?

There must be a better way! Thanks in advance for any advice!