Okay, I promised an answer. Sorry so long, I’m detailed. Here goes...
Bottom line, I will be moving my Outlook for Mac Calendar data manually, line by line, to my Exchange account. All 11,800-ish event lines. Here's why:
Stellar - The first thing that alerted me with Stellar was during our first chat about whether their converter would bring the Calendar Category with it, they immediately tried to move me from their $39 version to their $199 version, saying I would need that to get my data to Office 365. I knew better, as the PST file import to an Exchange Account in Outlook will do the same thing, therefore I didn’t need their $199 version for that specific purpose. I wouldn't mind paying $199 for a tool that would save me 60 hours of work, but they could not explain to me why the more expensive version would work better, nor did it offer better support. Meanwhile, they suggested downloading the free trial version first. So, I downloaded it, converted the OLM to PST, and imported the PST into an Outlook Profile I had set up for testing on the PC. The results were difficult to interpret at first. Not near as straightforward as another tool I tested later (Gladwev, next paragraph), plus it loaded ALL the calendar data (over 500 events) onto two dates! (The date on which I converted and the next day.) Obviously not acceptable. I contacted Stellar about this (another chat), asking them if this was due to the free version. Ultimately, after some time with them looking at the data, they said it was a ‘discrepancy” and that I needed to contact second level support either by phone or chat. Their time to contact is 8:00am to 4:00pm IST, which is 11.50 hours ahead of me. So in other words contact them at 8:30pm my time. Ultimately, I will not be contacting them.
Gladwev – After having a positive chat with Gladwev about my Calendar Category question, I thought I would try them. They were sure the Calendar Categories would convert, and they did. They had two alternatives, of which I could try both for free. They recommended Alternative 2 below, and after trying both, I see why. However, since I already had my OLM file located on the PC, I started with Alternative 1.
Gladwev Alternative 1: “Gladwev OLM to PST Converter Pro”, which runs on Windows. While both of their free converters will only show 10 converted results per folder converted, they initially show ‘all’ the files that 'will' be converted. INSTANTLY, I knew I had a problem. The Stellar converter above was a little murky about which Calendar folder you were looking at once the data was converted (I have several), and how many items per folder there were. However, the Gladwev converter INSTANTLY showed exactly how many events each Calendar folder contained. And that’s when I knew I had a severe problem. There were over 11,000 events missing! And upon further checking with an OLM viewer, they were NOT in the OLM file being converted. And after several tries, I realized that Outlook on the Mac was not going to give me those 11,000 events in an OLM file. So, end of testing for Alternative 1. And please note, ANY converter that started with an OLM file would not work. My data was NOT in the OLM! So no further testing needed on any OLM to PST converter.
Gladwev Alternative 2: “Gladwev Outlook Mac to PST Converter Ultimate”, which runs on the Mac. Notice, it does NOT use the OLM file! It actually queries the Mac database and creates the PST. And… it found my other 11,000 events! Yay! So I thought I might have the solution. Unfortunately, no. After a lot of importing the converted PST to PC Outlook and testing, I will not be using this product either. While this Gladwev converter is very easy to use, and much more straightforward and forthcoming than the Stellar product, ultimately there were many mistakes in my converted data. Too many to try to correct. The biggest was if the event was an ‘all day event’, it started the event at 6 or 7 pm the day before and continued it for 24 hours; therefore, the event ending up lasting for 2 days on the PC Outlook calendar! Not acceptable. And since at least ½ of my 11,800 events are ‘all day events’, it would take opening, correcting, and saving each event to fix the issue (I could find no easy way to correct). Also, some of my daily events had lost all their formatting within the notes of the event. Also not acceptable as some of my formatting indicates what I have accomplished for that day. While I REALLY liked this product, and maybe it is something they would fix, I have run out of patience in trying to find a solution.
So again, bottom line is I will be moving my 11,800-ish event lines one by one on the Mac from the “On My Computer” Calendar to the Exchange Account on the Mac. It will take 10-20 minutes per 100 events, but once they are there, they will be correct!
And please, if I ever again think Office 365 will run on the Mac like (as well as) it does on the PC, STOP ME!!!!!!!