For example, I requested that they pay my first rent payment, which was due June 30th. I submitted the payment request on June 27th. I checked with my landlord, and they received the check, as scheduled, on June 30th, and the funds were deducted from my account on June 30th.

I can understand your concern of not being able to tell whether it got there on time. Who knows if there’s going to be a mail glitch or something. So I now choose a date that’s a few days earlier than the true due date, the 27th of the month. That way it’s sure to be there on time even if the mail gets delayed. I agree that it’s a little nerve-wracking to not have confirmation of a payment.

I don’t really care about seeing whether they’ve cashed the check. In fact, even if I wrote them a check, it probably would take a few days to come back to my bank. And actually, I think this method is better. Once the check arrives, the funds are deducted from my account. This saves me the headache of having someone sit on my check for 4 months. I recently had this experience with the Rush Training Center, where they didn’t cash my CPR training payment until 3.5 months after I gave it to them and completed my training.

I agree that paying from the company’s site may seem a little easier, and sometimes it is. I still do that for a few things. I was surprised by how many companies can be paid electronically from Bill Pay though, and sometimes there are other advantages to paying with Bill Payments. For example, Schwab offers a few more options than Chase for paying my credit card bill. My credit card bill is automatically imported into Schwab, so the Payment Center knows how much I owe each month. In it’s online payments, Chase lets me choose to pay either the full amount or minimum payment on the bill’s due date. Using Schwab’s Bill Payments, I can choose to pay either the minimum payment or the full amount but I can pay either as soon as I receive the bill or on the bill’s due date. This works really well for me because Chase sends my bill about 3.5 weeks before it’s due, and I’d rather not wait that long to pay it. It also allows me to set a maximum, so that if my credit card bill is say greater than $1000, it sends me an email asking if I’d still like to pay the entire thing.

As for your technique for keeping track of due dates, I suggest you check out Ramit on automating your accounts if you haven’t read his book. A good automation technique will save you a lot of time and headache

My solution has been paying my bills directly from the company’s website. Most, if not all, have this option. The downside to this is that you actually have to remember when to log on to that side, knowing the log-on Username/pw. For the companies that don’t have this option, I set up an automatic withdrawal from my bank account. For the companies that do, I set up a google docs spreadsheet with due date, company, date I paid and confirmation number and notes rows as soon as the bills come in, I enter in into the spreadsheet. Creating a sheet within the file also has my Username/pw changed around a bit so not to make it too obvious. I (and the ppl I share it with) can check the spreadsheet and get a good sense of when each bill is due, what my bank balance should be, and what is upcoming. I also know exactly what day the funds are going to the drawn out of my account along the actual posting date so I never get a late payment. I never have to go back into my pile of bills to sort through and I always have a record as I copy and paste my monthly details plus conf. # into another sheet every 2-3 months. I can also look back at each month and see if there is a bill I missed or if it hasn’t yet been withdrawn from my acct yet. Also, I keep track of my checks I write as well and enter that in as a bill and log it in when it is withdrawn from my bank acct.
(I know this is waaaay to long of an answer, let me know if there’s something that doesn’t make sense)

JJ