I’m one of those old fashioned people who still pays most of my bills with checks and stamps. Which is bizarre considering how much I love the web. Mainly it’s thanks to inertia–it’s just been easier to do it the way I’ve done it and not bother exploring scary new options. But now that I’m going to be moving there’s the hassle of address changes and making sure all my bills still get paid. It seems an easy way to avoid that is to switch to online bill payment now.

But I’m wondering if it works well for anybody. Seems like the glowing future of online bill payment hasn’t quite happened yet.

I do pay my mortgage online, but haven’t done other bills because most of them I’d need to sign up for individually and suddenly I have a dozen different logins to keep track of. Yuck. (Though compared to what I do now this seems like the easiest option. I’d just need a cheat sheet somewhere with all the usernames/passwords)

There’s also the automatic payment option, but then you get lazy and don’t pay off a little extra on the loans or credit cards when you probably could. Plus the automatic payment can get scary if your budget is tight or your cash flow varies (like those of use who are self employed).

Then there’s the bill pay option most banks offer. My bank (TCF) has one, but I haven’t used it yet. I poked around with it and it seems overly basic. Almost like it was put together by non-techies. Or at least people who don’t really use the web. I haven’t exactly been thrilled with TCF’s online system–I set up notifications so my account balance wouldn’t get too low (again, cash flow is an issue for me), and twice those notifications just stopped working for no reason. The tech support guy’s solution was just to set them up again. Gee, thanks for instilling me with confidence.

My favorite part of TCF’s bill pay system is when they want to process all my bills–so I’d have to change my address to some goofy P.O. box in South Dakota. Sounds a little too goofball to me. I don’t think that’s required, but it seems like that’s how they want you to do it.

There’s also the Quicken/Money financial software that offers some form of online bill payment, which usually ties into your bank’s online offerings. Of course it actually has to work and it should be very cheap or free ($6.00/month isn’t cheap enough to break me of my checks/stamps habit).

And this all ties into how I manage my finances. I use financial software, but I’m basically keeping my own record and the bank keeps theirs and I have to input every single transaction. It’s maddening. But it does enable me to do budgeting (and see if we’re even close) and keep track of expenses for tax purposes. The software I bought is supposed to be able to sync with my bank, which would make all of that easier, but when I set it up it either cost extra or my bank wasn’t supported.

Seems like somebody somewhere should have figured out smarter banking by now. Let me track my statements so I don’t have to re-enter anything, pay bills electronically so I can save on stamps and checks and categorize everything–both so I can do budgeting and so come tax time I can tell the IRS exactly how much I spent on my utilities (home office deduction) and business lunches (deductible!). Either make it an online service as a part of my checking account or build it into Quicken or Money or whatever software you like. Seems like Google should be all over this.

So does anybody have an online financial system that works for them and doesn’t involve lots of extra work, a ridiculous number of logins or a backwards online bank system that doesn’t exactly ensure your trust? I’d love to hear what actually works.

Update: I’ve eaten my words and given online banking a try.