The world of personal finance software is one of my least favorite. Anyone developing in this market has a tough job. People are idiots, and personal finance itself is especially designed to cleverly imitate real accounting yet completely fail to make any logical sense at all.
So I am never surprised at the crazy junk I see in personal finance software. The system it targets is moronic in the extreme, and the target user is assumed to equal that standard.
But I'm a special idiot... one that uses Microsoft Money. I have tried Quicken, but I find their junk just a tad more annoying than MS Money but for different reasons. I also detest Qicken's license terms and marketing strategies. In contrast, Microsoft's lack of strategy in the personal finance market is quite refreshing. So I keep using MS Money even though I hate it.
The most annoying thing about MS Money is that they somehow makes it mandatory to upgrade to the new version every year. Somehow the old version just ends up "breaking" over time until you eventually get pissed enough to upgrade. I have no idea how they manage this, but eventually my old copy just sorta stops working right. Last time it was the fact that it wouldn't work after a patch for IE came out (and no fix available for the old version naturally). This time it just stopped being able to talk to my bank one day.
Every time I upgrade, I end up being amazed at how little was actually improved, or even changed from the previous version and equally amazed at just how many annoying "features" are still exactly as annoying as before. There always seem to be a couple of things I really like that manage to disappear from each version, and one or two new features show up that I don't care about at all. So each time I curse myself for forking over yet another $50 instead of just taking the time to put together my own spreadsheet in Excel... but I still I upgrade anyway.
Among my biggest complaints is the default "basic" checking account register. It completely lacks seriously important features, features I'd consider quite "basic"... like the fact that it is missing the entire right-click menu and has no obvious alternatives for useful things like creating a reoccurring bill from an entry in the register, or marking transaction as reconciled, etc. It is also not obvious that you are even in a "basic" mode, nor that there an "advanced" mode that you could be using instead. Sure, there is a "Basic Register" icon, complete with text label at the top of the page, but it blends in so well that I never even noticed it until someone pointed it out to me. The "basic" mode just make the application feel like a piece of crap that doesn't do much of anything.
Fortunately, I do know about advanced mode, despite not having noticed the icon. I know this because I had used older versions where the advanced features were enabled by default. When I first upgraded to a version with the "basic" register and saw that those features had gone missing, I located how to enable them again via the online help. But the "advanced" register isn't exactly "advanced". It just adds a few minor details to the list of transactions, turns on the right-click menu, and that's about it. But getting advanced mode enabled sure does requires an hell of an advanced level of skill. That icon at the top of the page isn't even clickable to toggle the mode! Instead, enabling the advanced register remains something that I have to look up in the online "help" feature each time because it is cleverly hidden deep within the not-so-fun "options" section of the program. Fortunately the online "help" is one of the few really well done parts of the application, and provides clear instructions for how to enable the missing functionality.
Then MS Money has the "basic" bills tracking system as the default too. In a misguided fit of "simplification", the developers of the default bills tracker helpfully allow you to choose to pay a bill using automatic payment (a.k.a. Bill Pay), electronic payment (e-pay), or by writing a check... But they thought that a "direct draft" bill was just too fucking complicated for the "basic" user, so that option isn't available unless you turn on the advanced bill tracking system. It's almost like they missed the fact that nearly every utility company on the planet pushes direct draft payment options like it was high-grade cocaine... Even people like me that prefer a push payment system over a pull payment system often end up with one or two drafts each month. In my case, some of my utilities actually give a discount if you agree to let them draft your payment. But, according to the crack MS Money development team I now know that only "advanced" users would need direct draft as a bill payment option. Thanks guys.
Then you have odd shit. Like the fact that, even in basic mode, MS Money encourages you to track your gross pay, taxes, withholdings, etc. from your paycheck. Most average joe home-users are obviously people that need to track the exact amount of their 401K deductions, but they would never need anything as advanced as fucking direct draft!
Anyway..
I find this "basic" vs. "advanced" thing to be a very obvious sign of poor UI design. After-all, it isn't as if there are THAT many "advanced" things you can do. Seems to be there should be just one account register, and just one bill tracking system. Then, by using good UI design, the software can helpfully arrange commands in a way that isn't confusing. The saddest thing is, the "advanced" register and bill tracking systems are actually quite easy to use once you figure out how to enable them. But most average joe home-users will never even learn that there is an advanced mode at all, much less get it turned on. Instead, most people would just think MS Money sucks and would not bother to use it... and, after asking around, this seems to be exactly what most people really do think.
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