Oct. 1: Boo! Welcome to the scariest month of the year.
Screenshot from GIPHY In addition to Halloween goblins, ghouls and hundreds of kids descending on your neighborhood at the end of this month, one of the scariest October items is that countdown clock a little higher up in this column. It's a stark reminder for millions of ultimate
procrastinators — No, I'm not one this year. Amazing, I know! — that their deadline to file extended 2018 tax returns is nearly over. Don't worry. I'll remind you again as Oct. 15 nears.
But why push the deadline?
Gather all the
documents you need to file your Form 1040, including 1099s and receipts associated with your
self-employment income, be it full-time or side hustle earnings. This
tax preparation checklist can help.
Oct. 4: OK. You're ready to finally file that Form 1040 before the 15th. Great! Now make sure you don't overspend to do so. Check out
Free File.
This IRS-tax software industry partnership program that provides no-cost return prep and
e-filing option is open for business through the October extension deadline for taxpayers whose income is $66,000 or less.
Oct. 10: If your job compensation includes
tips and you received $20 or more in gratuities in September, use
Form 4070 to report them today to your employer.
Oct. 14: So another week slipped by without you filing your taxes. No judging here. I've been there. The good news this year is that today is the federal Columbus Day holiday or, in many states and cities, now designated
Indigenous People's Day. If you don't have to head into the office, it's a great chance to work on your taxes. The IRS has some
final filing tips.
Oct. 15: It's here! The absolutely, positively final filing deadline for your 2018 return. Get your Form 1040 — remember, there's now
just one tax return under the Tax Cuts and Jobs Act (TCJA) changes — en route to the IRS today or you'll face
penalty and interest charges.
E-filers, whether using the previously mentioned Free File or a paid-for tax software package, technically have until midnight their time to hit "enter" on their computer keyboard. But I suggest you don't push that deadline. A late technical problem could turn into a costly late-filing issue.
If instead you're sending in an old-fashioned
paper return, check with your post office to make sure the envelope is postmarked today, the paper filing proof of timely tax filing.
Oct. 21: Now that your 2018 return is finally done, it's time to work on reducing your 2019 tax bill. By now, you're probably familiar with how the TCJA changed your tax filing and planning. But it never hurts to review your prior year's tax return, whether you just filed it last week or earlier in the year. It's a good foundation to look at what tax breaks you qualified for might be able to use again on this year's taxes.
Note, too, that inflation has upped many tax-related actions. The income tax earnings
brackets have been expanded a bit. So have the
standard deduction amounts.
And definitely look at how much you can put this year into tax-favored
retirement savings and
medical accounts. Not only can they help lower current tax bills, they could pay off in the future.
Finally, peruse the Taxpayer Advocate Service's
Taxpayer Roadmap.
This publication, designed along the lines of a subway map, shows the
stages of a taxpayer's journey through our elaborate tax system.
Oct. 25: Those retirement and medical accounts also are part of many workplace benefit plans. Since October is the start of the annual benefits enrollment open season at lots of companies across the country, it's a good time to carefully review those employer-provided perks, such as 401(k) plans and flexible spending accounts (FSAs) for both
health and child care purposes, to make sure you make the most of your options.
Oct. 28: With more than two months left in 2019, now's is the perfect time to set up your tax deduction
bunching strategy. Here you gather potential write-offs together into one tax year to ensure you have enough qualified expenses to meet some of the popular deduction thresholds. This typically covers the itemized deductions for medical, home-related and charitable deductions.
Oct. 31: What's scarier than the ghouls and goblins wandering your neighborhood tonight? Another month of the
hurricane season.
We've been lucky so far, with only Hurricane Dorian along the eastern seaboard and
Tropical Storm Imelda in Texas causing major damages. But with a month officially left, we
can't let down our storm guards.
The countdown clock below can help you track the days until the formal Nov. 30 end of the annual hurricane season.
You also can find tips on getting ready, physically and financially, for hurricanes, as well as tax help for recovery efforts and tax deductions for donations to those who are hit by natural disasters at the ol' blog's
Storm Warnings pages.
Small Business Tax Calendar: Important
filing, deposit and record keeping dates throughout the year that your company needs to know. You can get more tax calendar information at the IRS'
online calendar page and view the full year's important business and individual tax dates in
IRS Pub. 509.
Despite Texas coming in number one in this analysis, I'm happy to report that our school district tax rate
has dropped a bit from last year. So our combined 2007 property tax bill should
be a little smaller. 
I live 75 miles east of St. Louis in Southern Illinois, which is for the most part an economically depressed area. Med. Income around low $20's.
I live in a town of 16,000 people, and our property taxes here are atrocious. I have friends who have had their home on the market for 3 years, a lot of interested parties, until they see the property tax bill, no thanks. The homes aren't appreciating much in value either. My taxes for a 2900 sq. ft. home were over $8000. I could live for less in a City with a lot more to offer, than what I pay to live here. Our schools have failed to met the Average Yearly Progress for the last 2 years, yet the taxes increase every year, so I pay more and get less. As a point of reference, property taxes in the Chicago area, are on average less than in our fair city south. Less population = more taxes.
Posted by: MW - (Fed-Up with Taxes in Mousetown) | Monday, October 08, 2007 at 03:59 PM
Unfortunately this argument does not include state income taxes. Since state income taxes range from 1% to 4% of income (vs property value), it is difficult to compare apples to apples. What would truly be valuable would be a chart that compared the cost to live in each state for someone making $200,000 per year and living in a $500,000 home.
Posted by: Randy Walker | Monday, October 08, 2007 at 03:20 PM
The piece about taxes in Texas brought back not so fond memories of living in the Austin area. Currently, I'm in Key West and have a house roughly 3 times the value of my old house back in Austin. My current tax bill is still about $300 less per year than the TX house. I still maintain a lake house outside Austin and it's tax bill is about the same as mine here in FL. Like Texas, Florida has no state income tax and our sales tax is 6.5% so I'm not sure what makes up the difference or where the money goes, but it might be a good question to ask.
Posted by: Jeff R in Key West | Monday, October 08, 2007 at 02:48 PM
I live in TX (#1 on the list above), and my parents live in AL (#49 on the list). In fact I pay around double the property taxes they pay. That doesn't sound too crazy until you realize that I live in a 792 SF condo and they live in a 10,000SF house worth almost 10 times what my property is valued! But thank God I don't live in NY or NJ where people who inherit paid off homes are forced to sell because they can't afford the property taxes.
Posted by: Meg | Sunday, October 07, 2007 at 01:50 PM