The manual process isn't *that* hard. I've done it a half dozen times.
On the other hand, I also re-ripped my entire music collection from scratch when I started with JRiver MC. At first I maintained a library of medium quality AAC files. I then re-ripped each album in turn, deleting off the old AAC copies as I went. For me this was a good way to get to know my musical tastes again.
Ripping some albums led me to ripping others. As I got full quality copies of my music, it kind of expanded my musical world again. The process of ripping became a way of prioritizing things I wanted to hear again. I did the first pass of this over a period of about a week. This set me off on a journey to get back my love of music. Ultimately it led to me tripling my music collection (CDs) and really appreciating music again.
For my collection of 60 or 80 albums in AAC, I didn't bother to preserve anything in MC. I just deleted them and imported the new ones. There was nothing meaningful for me to keep. No playlists, etc. Didn't care about play history or anything at that point. This made it easier (no whacky replacement) and let me enjoy it. You probably aren't in this same situation but I thought I'd type this up anyway.
Best of luck,
Brian.