Hi David,
Nice work in getting Money 2003 running with PoL!
Below are some random thoughts, maybe one might help.
I haven't tried Money 2003 myself, I've only gone as far back as Money 2004 with Linux. The deal-breaker for me on Money 2004 was it didn't import my ofx files and I assumed it was an ofx version problem. (greater than 2.0?). Unfortunately I can't find where I had read which versions of Money support up to which versions of OFX. I thought it was in one of the docs list here:
It's possible I had the same problem in Money 2004 that you're having with Money 2003.
Something I do with Sunset running on Linux is install vcrun2005 from
winetricks. You might try that, or an older version of visual C runtime.
I think PoL has debug and log file features, you might be able to see
some errors when you try to import ofx files. I don't use PoL but
google should be able to get you in the ballpark.
In any case, in addition to running OFX analyze suggested by Cal, can you tell us what version the ofx files are from the headers in the files? I understand that they work when Money 2003 is running in Windows, do you recall any patches you might have installed in the past? Any registry tweaks?