Personally, I try to go to the latest version. I see it as participating in the development by helping find the bugs. Also, I have learned that getting too far behind in the updates can make for a difficult transition at some time--just as well try to keep up.
For an update procedure, one must be careful moving files from 2.xx to 3.xx, or for that matter with any update. The better way is to install the upgrade on to an old installation so that the files can be updated. I believe there were some changes between 2.xx and 3.7 which need changes in the files. The new version cannot just access the old data files.
Please note that Songs and Custom slide from a service will automatically saved into OpenLP. So if a service was setup on one system, then used on a different installation, what is in the song in the service will update the database. (Which is why we the portable system.)
In our setup, we run the portable version from a USB drive. My office computer and the sanctuary computers assign the same letter to the drive. I can then setup services on my office computer and then run them on the sanctuary system. We have two such drives and keep one as a backup. (Especially when updating versions.) The key is to keep ALL OpenLP files on the USB drive (media and everything) and keep the path consistent.
Next, watch between 2.xx and the most recent 3.xx version. The "start live items automatically" in the system settings is not working. You have to set the flag on each item when you place it in the service.
We use the Remote Interface extensively. (I use and Android table to run both OpenLP and OBS whenever we are short handed.) Anyway, I think it is between 2.xx and 3.xx that the remote interface changed "big time". It now uses Web Remote, which needs updated from time-to-time (though version 1.1.1 has been stable for several months).
Finally, I had trouble the other day running PPT. The one running the OpenLP system took the windows focus of off OpenLP and the Web Remote did not get the advance to PPT. (At least that seemed to be the symptom. )
Anyway, stick with 3.7 and get it working, if at all possible. (read up on the First Screen features in 3.7 )
Fred