This personal finance software comparison chart is a basic summary of what I think each software application has to offer.  In no way is it a comprehensive list of all their strengths and weaknesses so be sure to check out the full reviews by clicking on link at the right.

Please don’t over-analyze the order.  Each solution has it’s benefits and many of them are good at doing different things.  For this reason it’s somewhat difficult to put them in a numbered rank.  I do, however, feel that some shine above the rest and deserve to be placed near the top.

Rank Software* Price Strengths/Weaknesses Synopsis Review
#1
YNAB
$59.95 Strengths
-Very effective “YNAB Methodolgy”
-Envelope budgeting at it’s best
-Great customer support
-Fantastic new redesign
-Simple

Weaknesses:
-Some may want it to automatically update transactions.

YNAB 4 is the best personal finance application that I’ve found and the system that I personally use.  It uses envelope budgeting and the “YNAB methodology” to focus users on the tasks that will actually make a difference in the way they manage their money.  It’s simple, effective, and has saved me loads of money! My YNAB Review
Try YNAB 4
#2
Mvelopes
$10.80/month Strengths:
-Solid envelope budgeting
-Helps people managetheir moneyWeaknesses:
-Could use an update on look/polish
Mvelopes helps users focus on proactively managing their money rather than reactively telling them where the money has gone.  The envelope budgeting method is very effective and will help people save money and get out of debt. My Mvelopes ReviewTry Mvelopes
#3
Mint
Free Strengths:
-Free
-Great snapshot of current financesWeaknesses:
-Promotes hands off approach
-Not actively managing your money
Mint.com is one of the better financial aggregators that gives a good snapshot of net worth and your spending.  It doesn’t, however, promote activities that will help people effectively budget and plan for their expenditures and savings. My Mint ReviewTry Mint
#4
MoneyWell
$49.99 Strengths:
-Proven envelope methodology
-Solid softwareWeaknesses:
-Data analysis/graphs could use improvement
MoneyWell is a nice piece of Mac OS software that uses “buckets” to teach the proven envelope budgeting system. MoneyWell enforces the envelope system well, with the user interface being pretty intuitive. My MoneyWell ReviewTry MoneyWell
#5
Moneydance
$39.99 Strengths:
-Good PriceWeaknesses:
-Weak in budgeting
-A few usability tweaks would be nice
Functionally, Moneydance works.  If you can get past some of the minor usability issues and lack of polish, it’s not a bad tool to help you manage your finances.  I don’t, however, see a reason to use Moneydance over other options. My Moneydance ReviewTry Moneydance
#6
Wesabe
Free Strengths:
-Easy to use
-Interesting social aspect of financesWeaknesses:
-Reactive, rather than proactive, approach
Wesabe is a social network of sorts designed to use the “wisdom of crowds” to make better financial decisions.  It’s a good addition to, but not a replacement for, a solid software application to actively budget and plan for your finances. My Wesabe ReviewTry Wesabe
#7
Snowmint Budget
$39.95 Strengths:
-Solid envelope methodology
-Essentially bug freeWeaknesses:
-Data entry could be a bit faster
Budget, by Snowmint, is a solid contender among personal finance applications for the Mac. It uses envelope budgeting, which is great. The usability could use a little work, but overall a pretty good application. My Snowmint’s Budget ReviewTry Snowmint’s Budget
#8
iBank
$59.99 Strengths:
-Well designed
-Better than other Mac optionsWeaknesses:
-Weak budgeting area
-Useless coverflow view
iBank is a nice, Mac-based personal finance application that is much better than some other Mac options. It has some nice features and sync’s with your iPhone. I did find, however, that it’s budgeting section wasn’t as effective as I would have liked. My iBank ReviewTry iBank 3
#9
NeoBudget
$2.50/month Strengths:
-Solid envelope methodology
-Improving software rather quicklyWeaknesses:
-Usability could use a little work
NeoBudget is a web-based envelope budgeting system (which is an effective methodology for managing your finances).  While it is less expensive than it’s main competitor, it does lack some functionality for now. My NeoBudget ReviewTry NeoBudget
#10
CommonCents
$34.95 Strengths:
-Great envelope methodology
-Less expensiveWeaknesses:
-Usability needs improvement
-Not as polished as other programs
CommonCents 2.0 uses the highly effective envelope budgeting system. While the price tag is nice, the usability could use some improvements. With time and some improvements, CommonCents has the potential to be a very effective money manager. My CommonCents ReviewTry CommonCents
#11
Buxfer
$0 to$2.79
/month
Strengths:
-Basic membership is free
-Better budgeting than similar servicesWeaknesses:
-Budgeting still needs improvements
-Takes a more reactive approach
Buxfer is a clean finance app that offers a few innovative features as well many that you’d expect to see. You can store your bank info offline, track IOUs, and rollover your budget amounts. A basic membership is free, but in order to effectively budget, you’ll definitely need to upgrade, which costs. My Buxfer ReviewTry Buxfer
#12
Quicken Online
Free Strengths:
-Free
-Gives a good snapshot of financesWeaknesses:
-Weak budgeting area
-Not any better than other free apps
Quicken Online is Quicken’s response to the other popular web 2.0 personal finance apps. Unfortunately, they don’t improve on much and it ends up being just another basic financial aggregator. Nice Try Quicken. My Quicken Online ReviewTry Quicken Online
#13
moneyStrands
Free Strengths:
-Free
-Neat social appealWeaknesses:
-Weak budgeting capabilities
-Slower than other similar products
moneyStrands is a new and interesting model that gives personal finance a social aspect. Is it neat? Yes. Will it help you better manage your money? Probably not. It’s a bit slow and promotes a pretty backward-looking approach to your finances. My moneyStrands ReviewTry moneyStrands
#14
BudgetMap
$29.95 Strengths:
-Effective envelopes budgeting
-Very simpleWeaknesses:
-Requires manual recording and math
BudgetMap is a system of checkbook registers that help you to manage your finances through an envelope-type system.  Bottom line: it’s effective.  But some won’t be disciplined enough to manually record everything. My BudgetMap ReviewTry BudgetMap
#15
Geezeo
Free Strengths:
-An interesting social twist
-It’s freeWeaknesses:
-Editing transactions is tedious
-Weak budgeting functionality
Geezeo, like some other applications, is financial management with a social twist.  You can determine for yourself if this actually helps or not.  Functionally, Geezeo still needs some improvements (especially with the transactions and budgeting sections). My Geezeo ReviewTry Geezeo
#16
Quicken Deluxe
$59.99 Strengths:
-It has a large set of featuresWeaknesses:
-Horrible “forced” upgrade policy
-Not likely to actually improve your money management much
Quicken has a large set of features and automatically tracks your spending.  The problem? This doesn’t actually help you to better manage your finances.  It appears Quicken has improved their software, but not their system. My Quicken Deluxe ReviewTry Quicken Deluxe
#17
Money Plus
$59.99 *MS Money has been discontinued*Strengths:
-Capable, if you put in the timeWeaknesses:
-Not as effective/efficient as others
-Takes time to learn program
-Poor upgrade policy
Microsoft Money is a comprehensive money management program.  It’s quite capable of doing what you want, but you have a rather steep learning curve to get past in order to effectively drive the massive machine.  In addition, they have a not-so-customer friendly upgrade policy. My Microsoft Money Review
#18
Cha-Ching
$40 Strengths:
-It’s Clean
-Runs on a MacWeaknesses:
-Still has bugs
-Weak budgeting functionality
Cha-Ching 2 is a Mac friendly application that looks clean and has some interesting features. Functionally, it could still use a little work (transaction editing). While it will get the job done as far as tracking your spending goes, it’s budgeting section falls quite short of other solutions on the market. My Cha-Ching ReviewTry Cha-Ching
#19
MySpendingPlan
Free Strengths:
-It’s Free
-Uses envelope budgetingWeaknesses:
-Many Advertisements
-Slower than most
MySpendingPlanTM is a free, online application. While it uses envelope budget, the user’s effectiveness is weakened by slow responsiveness and too many advertisements. My MySpendingPlanTMReviewTry My MySpendingPlanTM
#20
Weekly Envelope
Free Strengths:
-It’s freeWeaknesses:
-Interface is cluttered
-Isn’t as effective as envelope budgeting should be
Weekly Envelope tells you how much you can spend to stay within your weekly budget. Unfortunately, I didn’t think the system was as effective as it could have been. In addition, the interface was cluttered and sometimes unclear. My Weekly Envelope ReviewTry Weekly Envelope
#21
Rudder
Free Strengths:
-It’s free
-It’s CleanWeaknesses:
-Simply isn’t effective
-Can’t edit bills?
Rudder is a system that emails you a summary of your finances each morning/week, etc. Aside from that (which isn’t much) it does nothing to actually help me better control my spending. My Rudder ReviewTry Rudder
#22
GnuCash
Free Strengths:
-Free
-Functionally powerfulWeaknesses:
-Not user friendly
-Difficult to use
GnuCash is free, but it comes with a different price: time and frustration.  Just to get started using it you’ll have to pour through enough documentation to make your head spin.  Bottom line: not user friendly and hence not very effective. My GnuCash ReviewTry GnuCash

*
Online = Online Software
Mac = Mac Software
Windows = Windows Software