Filing taxes: Anyone else as hesitant as me to pull trigger

I took a first crack at my taxes in August, which told me I needed to increase the withholding from our pension checks. I did them again in November, when I bought the latest tax software. That helped me determine whether I needed to do any year end maneuvers. (It also helped me find some errors in the H&R Block program). I did them again on New Year's Day, after all mutual fund distributions were in. I finalized them last week, after I had all the necessary forms in hand, as well as the H&R Block state program. I will owe $1400 total to the state and feds, and I will file on paper and pay in April.
 
I'm still waiting for Vanguard. The website says that 1099 Div should be out my mid February and it is the 15th! I'll probably wait until the first of the month to file just in case there is a revision.

I got my VG tax info. from their website and printed the tax form. (Accounts/Tax documents)

I always wait till the week before April 15th. to file, regardless. For the last 20 years we have NEVER got a tax refund and always have to pay them (Never had any penalties though). So I would rather the money be in my account and not the IRS'.
 
I mailed my paper forms on 2/1. By 2/5 the $41 payment check cleared.☺
 
I like that. That's a good reason. I'm not expecting anything else. I'll file it this weekend. Thanks.

is amending a tax return pretty simple or is it like a 1040 x where you have all kinds of paper work to send in by snail mail?
 
is amending a tax return pretty simple or is it like a 1040 x where you have all kinds of paper work to send in by snail mail?
Amend a return means you are filling out 1040X, and yes, you do have to snail mail it. TT makes it pretty simple, but there are a lot of forms to print and send. I've had to do it a few times but never because I got a 1099 or something like that late.
 
Got rid of REITs and LPs in taxable a few years ago.


I have 5 REITs in my accounts, about two years ago I either sold or moved all but one REIT over to non taxable accounts, because of this late paperwork hassle. I don't know why I didn't move this one that I have left. It pays a little over 9%, so worth having as a dividend payer, and added diversification. I might do a little research and maybe, get rid of this one too. I'm retired now and trying to make my income choices very flexible to help structure low taxes and to simplify tax time.
 
I’m with OP, I get forms entered in TT when they come in as anxious to see where I am with tax due or refund. 2019 had lots of moving pieces for us. Now I have all but one form from Fido, due this weekend so I should be ready Monday, but most of the time I back off at this point for a week or so, in case I remember something not entered and hit the file button late Feb or early March. Also worry about scammers filing with my SSN, but always something like that to worry bout :)
 
Just got our last 1099 in today. TT says we owe $142,549 so I will wait and send them a check in April.
 
I start my return as soon as I get the tax software and do a "preview" based on the the info I tracked during the year. As official forms come in, as as software updates are received, I update it.

When the final required form comes in (which occurred earlier this week) I'll walk through the entire form to double everything. If we are getting a refund I'' file by the beginning of March, if we ow I'll wait until a few days before April 15th to file.
 
Fidelity 1099-DIV came in today; went into turbo tax and imported data from Fidelity; finalized return; and submitted the return; took all of ten minutes. Amount owed was small enough that I didn't bother delaying payment until April. I then went into EFTPS and set up estimated tax payments for next year.

Taxes have sure become easy.

Marc
 
Just got our last 1099 in today. TT says we owe $142,549 so I will wait and send them a check in April.

I was wondering with DW if this was a typo. On one hand I would crap my pants if owed that much. On the other, must have had a really great year if that number is correct. Here is to ya !
 
Just got our last 1099 in today. TT says we owe $142,549 so I will wait and send them a check in April.

Impressive to owe that much and not have an underpayment penalty.
 
I usually do my taxes at the end of February. I had four different investment firms that handled my money, now I am down to two by design. It won't help me do my taxes any faster, but it's easier for me dealing with only two firms instead of four.
 
Usually file in March and pay in April. We have not received refunds for many years.
 
I make darn sure I’m not owed a refund.

I file when I can (have the info), but I don’t pay owed taxes until April 15 via eftps.
Since income has been increasing due to partial & then full year SS, I've made dang sure I don't owe penalty by paying 110%+ of previous year's taxes. Then there are Div & CG from funds variation. So far, 110%+ of 2018 doesn't look like it's going to be a big over-payment. This may settle down for 2020.
 
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I am waiting for 3 1099's from FIDO and another one. It is a function as to weather I am getting a refund or paying. I do not have a clue. Both DW and I sold some funds and I have no idea what the CG is going to look like this year.
My Fidelity 1099 has been available on line for a couple of weeks.
 
I'm just waiting for Fidelity. Absolutely positively no refund for me this year - same as the last 10 years. I guess I'm doing something right.
Depends if underpayment warrants a penalty or not.
 
My plan was 110% of previous year, but 2019 will be first year doing Roth conversions so it should be big total tax due
 
After I make a rough draft of my tax returns in late January or early February (after getting the last 1099), I put them away for a few weeks. When I look at them again, I then try to pretend I am reviewing them for the first time as a check on my own work. Also, a subsequent review I try to do differently, such as by hand instead of relying totally on my spreadsheet. Matching my previous work tells me I very likely haven't made any mistakes. Still, a third review in late March gives me more confidence I got it all correctly.
 
Since income has been increasing due to partial & then full year SS, I've made dang sure I don't owe penalty by paying 110%+ of previous year's taxes. Then there are Div & CG from funds variation. So far, 110%+ of 2018 doesn't look like it's going to be a big over-payment. This may settle down for 2020.

In years where I expect a jump in income compared to the prior year, I default to the 110% of prior years taxes safe harbor and then reevaluate for Jan Q4 estimated payment if it looks like I might end up overpaying.

BTW I haven’t paid any penalties at all, because I always meet the annualized quarterly criteria including paying at least 90% of taxes owed by Jan 15 of the following year.
 
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I got the 1099 that included my international fund on Jan 21.
Maybe Fido vs. VG? I got my VG 1099 with VTIAX before the end of January as well.
 
Just got notice that our last Fidelity brokerage 1099 is available. So DH will start downloading into TurboTax and get most of it done.

But what took them so long last year was the % foreign source income numbers. Needed that to complete our foreign tax credit forms.
 

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