The program is very functional. The following worked as expected:
What does not
There is a bug in the program such that it does not always close cleanly and leaves a process hanging. The program cannot therefore be restarted until this process has been manually killed.
It is possible to mitigate this in by going to Tools > Settings > Backup options:
Most times this allows the process to exit cleanly. Clearly, you may want to use another backup strategy such as online backup, setting up a cron job, or manually backing up.
In Money, one can press Ctrl+K to open the calculator but that tries to run the Windows calculator. If that's useful to you, you can run regedit in your wineprefix and edit HKCU\Software\Microsoft\Money\14.0\Calculator and set the value to your system's utility. For me, this is /usr/bin/gnome-calculator and this works.
What was not tested
I have not tested printing cheques or loan wizards and the like.
I am using the UK version available for download at http://moneymvps.org/downloads/files/2005/Money2005-UK-QFE2.exe
My setup goes something like this:
$ export WINEARCH=win32 WINEPREFIX=$HOME/.wine/prefixes/money
$ winetricks ie6 msxml6 corefonts
$ regsvr32 /i browseui.dll
wine "C:\Program Files\Microsoft Money 2005\MnyCoreFiles\msmoney.exe"
|Operating system||Test date||Wine version||Installs?||Runs?||Used|
|Show||Ubuntu 18.04 "Bionic" amd64 (+variants like Kubuntu)||Jan 12 2019||4.0-rc5||Yes||Yes||No||Garbage||junk_2010|
|Current||Solus||Jan 11 2018||3.0-rc2-staging||Yes||Yes||Yes||Silver||Rob Curtis|
|Show||Ubuntu 14.04 "Trusty" amd64 (+ variants like Kubuntu)||Apr 16 2016||1.9.7||Yes||Yes||Bronze||an anonymous user|
|Show||Ubuntu 14.04 "Trusty" i386 (+ variants like Kubuntu)||Nov 21 2014||1.7.31||Yes||Yes||Bronze||an anonymous user|
|Show||Ubuntu 12.04 "Precise" i386 (+ variants like Kubuntu)||Apr 25 2014||1.7.17||Yes||Yes||Bronze||an anonymous user|
|Bug #||Description||Status||Resolution||Other apps affected|
|32589||Microsoft Money 2005 Program Crash on Selecting Program Dropdown Box||UNCONFIRMED||View|
|32590||Microsoft Money 2005 does not terminate properly on exit||UNCONFIRMED||View|
|32880||Microsoft Money 2005-2007 crashes when 'File' menu is selected||NEW||View|
|36083||Microsoft Money 2005 Program Crash On Selecting "Portfolio Manager" Function||UNCONFIRMED||View|