It took me several months of trial and error to figure out how Mint worked best for me. My boyfriend started using it, a coworker and I discussed the program, and I convinced my college roommate to try it out as well.
I'm no technological genius (my boyfriend had to find my mortgage account, which didn't work quite right, and I wasn't creative enough to figure it out) so some of my problems may be due to not really understanding how to make the program do what I wanted, but here is 1) how the program works and 2) some things I've found that work best for me.
Mint has a user-friendly interface with tabs across the top of the screen.
The Overview shows each account down the left side of the screen, totalling for your net worth at the bottom, and then a summary of trends below. The right side shows alerts, then your budget and current progress (there's even a handy bar that shows how far through the month you are), then goals, then investments.
The next tab is Transactions, which shows all of your transactions from your linked accounts. It auto-categorizes them, but you can change it. This is helpful if a) it guesses wrong and/or b) you would prefer not to use certain categories. This is mostly a checking-in screen for me. I can see everything I've been spending and make sure its putting it in the right place.
Moving along, we come to Budgets. I have way more to say about this, but the short version is you can set up budgets in any one of a number of categories (home, auto, food & drink, etc).
They recently added the Goals tab, which isn't useful for me, but I tried it and helped a friend set it up, so I have a decent handle on how it works.
Trends is great fun. It lets you make all kinds of different graphs, beginning with a pie chart of your spending for the month, but also letting you make bar graphs over time, compare categories and much more. Now that I've had my account for awhile, this is also helpful in refining my budget--at the bottom of the screen it gives you least spent, most spent and average.
Last is Investments, which looks fascinating, but I never use. My investment accounts are the way my uncle the financial planner told me to do them, and I'm not planning on messing with them, so I don't track their progress. Bad Mary. Oh well. I do add to them though.
Oh, and I guess last-last is Ways to Save, which I'm pretty sure is just advertisers, but is maybe helpful if you are paying fees for your bank or credit card (which I'm not).
If you're still with me...here's my experience:
I set up my account a year ago (teacher with too much winter break free time). This takes awhile, as you have to input the logon data for each account. I have 11 accounts, some of which I don't log in to particularly frequently, and some have syncing issues. For instance, my mortgage, through Bank of America, isn't accessed by selecting Bank of America. You have to look up "Mortgage Bank of America" or something to get it to sync correctly. Although I occasionally have compatibility issues, I have access to all of my accounts.
There are two big things Mint will help with: aggregating all of your financial information and letting you easily match it to your budget. Once it's set up, logging in to Mint shows you how much is in each account, and what your spending is in each category. The historical stuff won't be useful for awhile, so to start with, set up budgets. Go under the budget tab and set a budget for whichever categories you choose. Mint has 21 categories, most with additional subcategories. (So under "Auto & Transport" there's auto payment, auto insurance, parking and transit, among others). You can add any additional categories you want, although you can't change or delete their predetermined categories.
Make your best guess for each one--you'll probably be wrong, but thats ok. You can change it whenever you want. I initially set up a budget with about 20 categories, which wasn't right for me. I'm not a big spender, so breaking out food more than "groceries" and "restaurant" was annoying--but if you stop for fast food and frequent coffee shops, that might be a distinction thats helpful to you. For me, categories I had really low spending in weren't helpful, or things that were minor and infrequent (like stamps). Those take awhile though, so for now just:
1. Enter your information to make your account.
2. Set up a "guess" budget.
Login once a week or so to look over your transactions and re-categorize anything incorrect. Mint does it for you, but although it always knows "McDonalds" is fast food, it can get confused about businesses with unclear names, like "Ringo" so you'll need to change it so it knows its a restaurants. Don't bother messing with your budgets yet!
Have you tried Mint?