The problem that I see in the wine-install-no-chmod is:
The following packages have unmet dependencies:
wine-stable : Depends: wine-stable-i386 (= 11.0.0.0~bookworm-1) but it is not installable
E: Unable to correct problems, you have held broken packages.
So the rest of wine was uninstalled previously but the i386 package was not, and that was muddying the waters.
I can see in the wine-install-no-chmod that neither a wine prefix was created nor did winetricks run on the wine-install-no-chmod attempt. Effectively, the required pieces weren't in place yet to succeed. At the very bottom of the log file it says:
cp: target '/home/dmkimber/.msmoneyprefix/drive_c/windows/syswow64': No such file or directory
./Install.sh: line 533: wine: command not found
So if you look into the wine-install log that worked, you'll see that it installs the rest of the missing :i386 packages that didn't make it the first time around.
I think it was a lucky coincidence that running Install.sh a second time worked after the apt inconsistency resolved itself.
I don't think running Install.sh or MSMoney.sh in different displays should matter, maybe a spurious wine glitch?
So maybe if you want to give this another go, either run the Uninstall.sh in the msmoneysetup/.uninstall folder or run:
$ sudo apt uninstall winehq-stable wine-stable wine-stable-amd64 wine-stable-i386
and that will remove all 4 parts of wine.
Then do the chmod -R u+x ~/msmoneysetup and run Install.sh.
(I don't understand why the executable permission is removed/disabled, maybe some kind of google/chromeOS security?)
I run Install.sh all the time in testing so it really should work completely the first time, assuming permissions are good.
If we can figure out why ChromeOS acts like this, then Install.sh should run consistently for you.
I’m glad MSMoneyquotes works for you! PocketSense is probably not as robust as it could be considering that it was created for python2 and with community best efforts to convert it to python3 it isn't perfect. With Direct Connect being phased out quickly now, I wonder how useful pocketsense will be going forward. If you look in msmoneysetup/desktop there is a OFXQFX.sh script that looks in ~/Downloads and tries to import any qfx and ofx files after backing them up to statement.ofx.bak and scrubbing problems (currently for my penfed and nfcu files). This is very rudimentary, it doesn't combine them into one ofx file; just processes them one at a time and sends them to Money.
As for Balance your account, this doesn't work with Money prior to Sunset (2008) in wine. I've tried, and continue to test anything and everything that I can think of.
If you Balance an account while in the process of running Install.sh when Money runs for the first time, it should work.
If you do it when running MSMoney.sh, Money will hang and you'll see this in the log:
0190:err:sync:RtlpWaitForCriticalSection section 003FEEC8 (null) wait timed out in thread 0190, blocked by 012c, retrying (60 sec)
Money is stuck in a deadlock. One process needs access to some exclusive resource but something else won't let it go. You have to Ctrl-c to get out of this.
You're a pioneer in the Chromebook space David! Hopefully with more of your feedback we can adjust Install.sh to be more compatible with ChromeOS.