#1 (MUSIC HOLD FILE SIZE ISSUE)
I had the same problem where I had an mp3 that was slightly under 5MB; 4,853KB to be exact, and it did NOT want to upload; it kept saying the file must be under 5MB, and it was.
Thankfully we have all the software to reduce the quality and maintain the length of the file, either way, we reduced it to 4.5MB and it still didn't work, we brought it all the way down to 4.1MB in size for it to upload, exactly 4,187KB.
I was very upset, we reduced the quality of the audio file from 128kbps to 96kbps and it was noticeable.
#2 (CALL ON HOLD GOES BACK TO THE BEGINNING OF THE TRACK AGAIN AND AGAIN)
On the subject where THE CALLER GETS THEIR HOLD MUSIC TO LOOP, BUT ALSO REPEAT FROM THE VERY BEGINNING EVERY TIME THEY ARE TAKEN OFF HOLD AND PLACED ON HOLD AGAIN AND AGAIN, THE TRACK WOULD GO BACK TO THE BEGINNING, not allowing the caller to listen to your crafted company motto, company message, advertising of your products or your recordings in the studio over the hold music saying why our services are better than the competition etc... In contrast, other "music on hold" from competitors such as Vonage Business etc, allow the caller to listen to hold music and if taken off hold and placed back on hold, the caller stays in the same place (minute and second) of the hold music, thus right where they left off... It is true however, ALL SYSTEMS, competition or OOMA, that if they stay on hold long enough the track will eventually loop/repeat, if you have that option selected, if not, some systems, not OOMA, will go on to the next track (allowing you to have more than one hold track sequentially [Vonage for example]) even allowing you to have a "random track pick" when placing someone on hold as an option... This is not a special feature, these are STANDARD FEATURES, and these features are old, like 2005 old, I've been thru quite a few phone systems as an admistrator. OOMA is great, but it is behind in that aspect for sure. Best value though... OOMA, we believe they will improve.