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Info from Drew (stolen directly from his post on the lst help forum [1]
Updating the CMP sets*shouldn't* be all that hard, *if* done in a methodical
manner and using thetools available.
If the sets you have are working fantastic in 5.14, then you should be able to use the converter program available in 5.16 to bring those sets forward with minimal fuss - that was the purpose of the converter - to assist homebrews and older sets to stay current.
From my own experience in keeping sets up to date the issues the converter isn't able to handle is improper syntax that 5.14 was silently dropping. With 5.16 we have greater error catching than before. The error catching improves even more as we progress into 6.0.
Here is what I recommend - You run the PCGen Converter. It will have a LOG of issues it couldn't handle - look at those and fix them.
Load up 5.16, Open you preferences - Find the Input - there should be a check box to select 'Show Detailed Error Report' or something along those lines. There is also the option to turn of deprecated warnings - I'd recommend unselecting that so you can fix the true errors first, then we'll worry about updating the syntax.
Next - Load only your core set (PHB) (I prefer to use the bat file to load pcgen which has a dos console box open, but you can simply open the console in pcgen under tools IIRC).
Note the Error Messages - If in the dox box select all the text and then hit 'ENTER' - that will save all those errors (I usually open my text editor and place those in their own file - errors.lst.
Deprecated/Deprecation Messages should be safe to ignore for now - In fact if you followed the above, you shouldn't be seeing them.
Unconstructed References - These are Abilities, Feats, Templates which are being asked for that the program cannot find. It will tell you what Category 'Feat' 'Special Ability' etc, and the name of the offending file. It should also give you the originating file for the call. Though that may be later in 5.17 we got that ability. In most cases you either have a typo (Misspelled name, or someone isn't using the KEY name if it's set). Fix those by either correcting the typo, or in the case it's actually missing, create one.
Error Messages are the big issues - You've got syntax usage in a wrong file, or improper usage of syntax. It will usually tell you the file, and the offending syntax, in some cases you'll have one issue generate 2 to 3 warnings, since once one part of the syntax is bad, the rest is also bad. These need to be fixed for a smooth operation.
NPEs - NullPointerErrors - Those are the SERIOUS that severely broke something - DO NOT CONTINUE TO USE PCGEN if you see one of these errors - any issue you find is NULL & VOID as the program is already broken and unstable. These need to be addressed immediately. Fix it, restart PCGen and try again. Common causes of these guys - Spaces where spaces do not belong; stray symbols in odd places, or really bad syntax. In all cases, you should seek help on the lst help forum as any of the code monkeys and experienced Data Monkeys can usually discern what the cause is and direct you how to fix it.
Other weird error messages - You either have a Code Issue, or your syntax is funky. Report it here. Unlike those nasty NPEs, these guys mean you broke something, but the rest of the program should be okay to use (i.e. your broken issue is isolated from the rest of the program).
Like I said before, most of your error messages won't be the fault of the converter, it was bad syntax that was never discovered till the program was taught to announce it. It may seem like a mountain, but be methodical - Trust me, most of your errors can be caught at load up without opening any character. I'd say give yourself a couple of hours and most if not all your issues can be fixed.
