[editors note: this was written a few seeks ago, but there were website issues preventing timely posting.]
I hate doing my taxes. Not paying taxes – that I don’t really mind. I recognize the need to contribute to a functioning society. But doing the taxes, filling out the paperwork and submitting it?
Fills. me. with. dread.
I’m always certain that, if the sheer frustration of the nonsensical forms don’t kill me, I’ll screw it up and inadvertently commit tax fraud. And go directly to federal prison for life. Though I hear the food isn’t that bad.
Wildly irrational, I know. But, still, dread.
So, I’m of the mind that paying someone who doesn’t despise this down to the very core of their bones to do the taxes on my behalf is a worthwhile investment of my money.
I made the appointment and gathered up all my forms. And arrange to take a little time off of work so that I could arrive early – no stress, right?
On the day of, I’m a few minutes early and have my folder neatly ready to go with all the forms. The Tax Guy comes out and I find out that they aren’t doing in-person appointments anymore – COVID – so my appointment was “drop off and go”.
Now, I had planned on being done with this mess that day. Even had stamps with me to mail in my city taxes on the way home – and my checkbook for the direct deposit. I was ready.
Instead, I scrambled to give the guy my info and the big events – bought a house, sold a house, got married (but filing separately). He jotted down some notes, took my paperwork, told me they would have this done in a few days so I could pick things up and pay…
…And then sent me on my way.
Instead of being done, I had to wait. And, you know, dread.
A few nerve wracking days later, I got a call and set up another appointment to pick things up.
I get there slightly early, but there’s clearly a problem. There’s only the one Tax Guy there and no receptionist – or anyone else He’s running late as a result.
50 minutes after my appointment was to have started, he comes back to the lobby to bring me back to his cubicle.
And we proceed to go over most of the information that was already entered into the computer. Not sure how this was the wrap-up but whatever – he offered to give me a discount since I had to wait so long. And hey, this is the guy keeping me out of federal prison. I figured I could cut him some slack.
But there’s another problem – I’m missing a form. A 1099-S form for the Sale of Property. I should have gotten that from my bank that held the mortgage on my house that I sold and paid off in 2020. I have the Interest Paid form (1098, I believe), but no 1099-S. He tells me that it “shouldn’t” make a difference since I won’t owe taxes if I had lived there more than two years, but I still should have it and can drop it off later if I find it to file an amended return.
The rest goes normally, I pay the slightly reduced fee and head home to dig through all the paperwork again – and drop off the city forms in the mail. At least I got to use that stamp.
I tear my files apart when I get home, but no 1099-S form is to be found. So, I go online and make an appointment with my bank for the following Monday at lunch time to see if they can print one out.
On Monday, I get a call to confirm the appointment and they ask what I needed. When I tell them about the form they immediately reply that they don’t do anything with the mortgage stuff – and we cancel the appointment.
I did get a number from them to call the mortgage wing of the bank and called them next. After wading through the menus, I finally get to a person. I explain what I’m looking for and they have to put me on hold.
10 minutes later they are back – but no help. I need to get the form from the IRS website and then I can fill it out based on the interest form the bank did send me.
Fine.
Next stop, IRS website where I find the form – with a note that says if I actually print this out and send it in it won’t be scannable. THERE WILL BE A PENALTY. Instead, I have to order it and they’ll send it in the mail – in 10 business days.
So, I order the form and the instructions sheet and wait.
10 days later, I get the envelope from the IRS. The instructions and the form itself are horrible – the least clear thing I’ve ever read. They also included another form that has to be sent in with the 1099-S for some reason. It ‘suggests’ that whomever handled the transaction should complete the form on behalf of the seller. Okaaay.
With the bank and the Tax Guy really no help and me not having a clue how to proceed, I take another desperate stab in the dark. The title company had a ton of paperwork and seemed like they knew what they were doing – and might count as the ones who did the transaction. I find the email of the Title Guy and drop him a note. And wait.
The Title Guy gets back to me to clarify. He recognizes the form name, but indicates that I don’t have to file it since this was my primary residence. Quite clear and quite helpful.
This matches up mostly with what the Tax Guy said, what I read on a not-official tax site, with the confusion from the bank (sort of), and mostly with what little I gleaned from the forms.
With the refunds already in my account, I package all the notes and paperwork back up and resolve to stop worrying about it.
For another year, at least.