I'm also considering finally making a move to Apple Music...I've subscribed to iTunes Match for many years. Any tips on things to do/things to avoid in making that transition?
I highly suggest keeping at least one back up of all your music, even more so if you plan on going to Apple Music. If something happens to your cloud stored music, there is a good chance that Apple won't do anything for you.
I have used iTunes Match since launch and have overall enjoyed it, although, I hate that Apple removed iTunes Radio from Match Subscribers, but overall, it has been good.
The biggest issue I had was back in 2015 when Apple Music launched. A lot of people were finding out that their libraries were being replaced or disappearing after the AM trial was over.
I had my iTunes music library disappear on me, and I didn't even do the AM free trial. All my songs were greyed out on every Apple device that I had.
I called Apple Support, but they couldn't help and elevated the issues to the Apple Engineers. A few weeks went by and I called to get an update, and Apple Support read the engineer's notes stating that I never had any music upload using iTunes Match, which was of course bull crap.
Luckily, I had a back up to almost every song.
Now that I think about it, I feel like 2015 was the first year where I started to have a crap load of problems with Apple products and services. I talked to Apple Support more in 2015 that I did the prior 20 years of using their products.
I think overall, Apple's quality has gone down hill over the past 5-7 years.