You got 2014.5 to run in Mojave? You're doing way better than most. We've heard of a very few running legacy installs where it still worked after an OS upgrade. Mine was not one of those machines. There's about a 100% chance that moving it to another volume will cause it to not work—it won't install.

2014.5 will run over High Sierra with some functionality crippled. I don't recall if it will install or if you have to do that over Sierra and upgrade the OS. That was so three years ago.

In other news, Finale owners get a special price on SmartScore 64, just released. 

https://makemusic.zendesk.com/hc/en-us/community/posts/360049185894-SmartScore-64-Released-finally-Music-Scanning-App 

Focus on what you want to accomplish and not how you want to do it. 

Thanks for the reply. I've had no real problems that I notice running 2014. Guess I'm lucky.

As for SmartScore, I only scan a couple scores per year, usually to arrange for marching band, so the $99 is still pretty steep. I might just decide to install Catalina to the new volume and move everything but 2014.

But, if I were to spend the money or get my music boosters to foot the bill, do I get SmartScore or music to XML? Is there a difference in workflow or reliability?

You can think of Music-to-XML as the 64 bit version of SS Lite. In fact, it was supposed to be bundled with 25 until publishers complained about copyright and it was pulled out at the last moment. Though it has more functionality, you still cannot edit the scan except in Finale (or other notation app which SS-L couldn’t do). There’s no demo but Musitek will convert a scan for you in pre-sales.

SmartScore 64 is the successor to SmartScore X2 Pro and lets you edit the scan before export which many of us prefer. You also have a number of export options. There’s a 30 day demo. 

Lite has worked OK for my purposes, but fixing the mistakes does get to be difficult or sometimes impossible with how that data isn't always manipulable once in Finale. Does XML do a better job with the initial scan than SS Lite, or do I need to go to the 64 to get better accuracy?

If you don’t like the inability to fix scans in SS Lite, you might not care for the fact that M–MXL imports a lot more data that will have t be edited.

Just a guess — we are not you..

Again, there’s a demo for 64 and Musitek will do one scan for free but there’s a 3rd option: If you purchase Music-to-XML desktop and decide that you really need 64, there’s an upgrade option.

https://www.musitek.com/store/UpMusicToXML.html 

If you do the math, it’s a wash — same as if you’d upgraded to X2 Pro earlier and upgraded to 64 from there or go directly to 64 from Finale. Again, we are not you.

As for myself, I didn’t like SS Lite so I had zero interest in Music-to-XML.