I think stief made some wise suggestions, a couple perhaps you should consider more seriously:

"...but like Adobe and even Apple, LW is considering dropping OS 9 support since Java has changed so much."
"btw--if you're running 9.2, I think that means your machine can run Panther."

On your machines you can have both OS9 & X installed giving the options of which one to start up from. And in any case, Classic environment (OS9 under the control of OSX) would also be available. OSX's RAM management is very efficient. If any app crashes, it won't crash the computer, but that RAM becomes isolated & you can force the app to quit & restart the app.

OSX has more recent Java which is extremely important to LW. Do you have the most recent Java version for OS 9 (is that OS9.2 or 9.2.2 you have?) Having the most recent OS 9 version of Java will most likely benefit LW. The OS 9 Java issue has been discussed very recently on this forum. There's a link to where the download site is but I can't remember which thread it's in.

Unless you're totally happy with things in OS 9, you should give the OSX more thought! (How's the HDD space going on your comp.s)