As a small business owner, I don't have to issue a lot of people 1099s. Two to three dozen a year. It's not complicated, really, though it has often been annoying, since the forms are expensive, not always easy to find in stock, and you have to mess around with the alignment to get them to print right. So I was pretty excited by the idea of eFiling the 1099s and then being able to print them on plain paper. At $39, it seemed reasonable. At the "early bird" pricing of $25.00, it seemed very reasonable. Though, to be honest, you do still have to mail them. So you have to buy envelopes especially for 1099 forms. The motivator for me is that this year I have to mail exactly 25 of them and the forms are sold in batches of 25. If I mess one up or have to reprint at all, I'm going to need another batch. But if I pay for this eFile service, I can print them as needed on plain paper. So that's a bit of insurance for me, I guess.
In 2012, QuickBooks introduces a 1099 "Wizard." Alas, this is more like those stories where the wizard is a bumbling idiot than all-powerful. The wizard, according to Parvinder Makkar, the tech support rep I spent four hours on the phone with over two days, is still "a work in progress." I'd call it a kludge.
As mentioned in a prior post, the IRS will, apparently, now receive data from credit card companies and PayPal. So if you, the small business owner, pay a contractor (say a plumber) with a credit card, the IRS will be able to track that payment from you to the plumber. So you need not issue a 1099 to the plumber. Or let's say you hire a graphic artist and pay that graphic artist via PayPal. Again, no 1099 need be issued by you. Or least, this is how I understand it from QuickBooks. So QuickBooks needed a way to let you include or exclude which payments you made to contractors should be included in 1099s. Let's say you paid that graphic designer by check one job for $800 and by PayPal another job for $900. The 1099, as I understand it, should only reflect the $800 payment. But if you use PayPal and allow direct debit from your checking account, then you could, conceivably, use the Check form and your existing checking account to show that payment. This could screw up your 1099s. I, for one, have a separate account for PayPal in QuickBooks and I generally only make PayPal payments with my credit card. On the rare instance where I have a balance in my PayPal account, that gets used, but that's happened, literally, once. So if you put transactions via PayPal directly into your check register, you now need to use a "code" that QuickBooks will pick up so that it knows not to include that transaction in the 1099. Confused yet? Well, it gets better.
The wizard requires you to step through and ultimately review "included" and "excluded" transactions, after which you finally get the point where you can either print the 1099s or use the eFile service.
But the Wizard was returning completely erroneous data. It said I maybe owed two people 1099s, not 27 (and it did seem uncertain about those two) as per the 1099 Detail Report. And after two hours of letting "Vic" from Intuit review my transactions with his supervisor via connected support (meaning they took control of my computer and left me twiddling my thumbs), they decided that I had found bug #2 for the day. Yay! I'm not a lunatic. I didn't have a corrupt file. And I wasn't using a totally worthless piece-of crap software program. Oh, wait. Well, two of three ain't bad.
So, here's what they told me. I use a lot of "expense items" as shortcuts to include information on client checks, i.e., I created items for things and entered descriptions, so that the descriptions appear on the checks. An example might be "Bank Charge" as an item and the description might be "Bank Service Charge." Well, apparently the QuickBooks wizard doesn't see "through" those items to the underlying accounts. Had I used the account for Bank Charges under the Expenses tab, rather than an item on the Items tab, it would have worked fine. But it does not. However, I was reassured that my 1099s would print correctly because the 1099 Detail Report was correct. And I was assured they would send this whole mess off to the developers to address in a future release.
Alas, I am unable to find out, because when I tried to use the service, it insisted I sign in and then choose my company. Two "The Zack Company, Inc." files appeared to exist in their "App Center." One had a number next to it (presumably the one that was already syncing) and one did not. I tried to choose the one with the number. It insisted I had to be logged in as an Administrator to use it. Of course I was logged in as an Admin, so what was the issue? I have no idea. On a whim, I tried the other version next. This kicked me to a help screen that instructed me to "enable" the Sync Manager. Only problem? It was already running.
So I decided to try it all again, from scratch, but I had an email from Intuit thanking me for signing up. This had a link. I tried the link and it is stuck on directions to enable syncing, which is already enabled. Trying to go through the process from within QuickBooks just ends here:
If you can't read it, that's an error message saying "The page you have requested does not exist." This results from using a button from within QuickBooks and using its internal browser. I didn't input a URL; I just pushed the button.
So it appears, really, that I am three-for-three and have found yet another bug in QuickBooks.

This is really very nice article
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