I've used quite a wide variety of money management software and technology. I started out with just my checkbook which worked out great when all I did was pay my phone bill once a month, textbooks once a semester, and ordered the occasional pizza. It didn't take long after getting out into the "real world" that I quickly realized something slightly more advanced would be needed. For a while I used a spreadsheet created in OpenOffice but once you get above two pages or so of transactions, that becomes fairly cumbersome.
I'll save any of you who are Mac users with a simple amount of finances to track some reading: if you have one checking account, one savings account, and one credit card or a similarly simple setup, check out Cashbox - it is free and open source and will most likely do what you want it to.
Soon after, I discovered personal finance software. gnucash worked great for quite a while once I got it installed. If you use Linux or MacOS/X and want a full-featured financial application for free, give Gnucash a try. It may be overkill for some people. Also, a word of warning: don't try to install it without some kind of package manager such as apt-get on Linux or fink on OS/X. You'll spend hours trying to install all the required pieces of software it depends on manually. On OS/X, you'll need to install X11 first.
Gnucash worked out great until I upgraded my Linux install and it dropped gtk1 support in favor of gtk2, and I couldn't get it working again. And that is when I found Moneydance - my current preferred personal finance app, which I'll cover in detail later.
I used Moneydance until I bought a Mac, which came with Quicken 2002 for the Mac. I upgraded to Quicken 2005 for Mac thanks to a mail-in rebate that came with TurboTax. At one point, I started noticing some stability issues with Quicken and decided to go back to Moneydance.
Moneydance is written in Java, so it works (in theory) on any computer that supports Java. They officially support Windows, Mac, and Linux. I used it happily for over a year and then had a thought: I'm using the envelope system for budgeting after going through Dave Ramsey's Financial Peace University class, why not use the envelope system for EVERYTHING? Enter the program known simply as Budget.
I purchased a copy of Budget because I was not happy with the way Moneydance did budgeting. It was $29.95 and came with free upgrades for life. They have a very active and helpful community and developers who actively answer questions on their forums. I just found myself not keeping track of my money as well as I had with Moneydance. There was just enough additional complexity that to me, it started feeling like more of a chore to keep track of my money. When you're used to a checkbook, the jump to using envelopes for everything was just too much of a mental jump. Maybe if I used it for a couple months more, I'd like it better, but I've got better things to do with my time.
I ended up purchasing Cha-Ching - a very promising looking program still in beta. They also boast an active forum with users supported each other and developers jumping in to answer questions too. Unfortunately, the budgeting part of Cha-Ching is currently completely unusable, making Moneydance or Budget seem like better options once again.
Just to put a weird spin on things, not two weeks after I bought Budget AND Cha-Ching, Moneydance 2007 becomes available as a free upgrade to anyone who purchased Moneydance after January 2004. So after I spend $45 for Budget and Cha-Ching and then a few hours messing with the two of them - here's the software I already use and really like is updated and the updates include enhanced budgeting functionality. If I had just waited a couple weeks, I would've saved time and money.
To keep this post from getting too long, I'm going to split off the descriptions of what is new in Moneydance 2007 into a different post.
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