Just wanted to weigh in here to see if I could supply any useful info. I have been a Linux user for a long time and have just switched to Strawberry from Guayadeque, which is no longer maintained. I have a CD collection of about 1000 discs so I like to be able to sort things to my tastes to make searching easier
I have never used my music player to rip - maybe since you are coming from IOS that might be a feature of iTunes which is something you are used to? I have no experience with IOS except for a brief ownership of an iPod that totally rearranged my mp3 collection. Apple has there own way of doing things...
I have always used another program to rip my CDs. A portion of my CD collection had a been ripped on Windows using Exact Audio Copy (I rip everything to FLAC) and later imported those files into Linux. Up until Strawberry it had been a bit of a mess, mostly due to genre tags being inconsistent and wonky. I have been updating my collection with the recent change to Strawberry and things have never been neater.
Here are some Linux tools that I use to rip - Asunder, RipperX. I don't mind ripping with a different program, it allows me edit and check the files before they get added to my main collection
The collection editor built into Strawberry is powerful (right click, edit track information...). You can batch edit entire artist folders as well as individual albums and tracks. There is also an auto complete function which uses some database (not sure which) to fill out all fields. This may help.
In the "re-grooming" of my CD collection I have also been using several Tag editors. Puddletag is awesome, Kid3-qt is also useful. Picard Music Brainz may help in look up and auto-fill a but it's not super intuitive. Again, as I am finishing up sorting my CD collection I am just using the editor in Strawberry.
I am a new user to Strawberry like you and I am very happy with it so far, it does a lot of things really well - check out Smart Playlists. The only thing I miss is browsing via cover art - in Windows I used Album Player and in Linux I used Guayadeque (Lollypop is another cover art based player but I had issues with genre tags that made it unusable).
Finally, just a word of caution: you may want to drag a few of your collection folders to the desktop to experiment before going at the full collection.
Hope this helps you get your music sorted.