Do Everything Else

Taxes: the Good, the Bad, and the Ugly

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One of my worst traits is procrastination. Ever since high school, I have had a tendency to put important things off until the last-minute. I thought maybe I could grow out of it, but lo and behold, as an adult, I find myself doing the exact same thing. However, being an adult, some things that don’t get done by a certain deadline can have serious consequences…like taxes.
As everyone knows, yesterday was tax day. April 15 is a date James and I knew about and used that as our deadline to get our taxes done. So, of course, we just put them off until the last…possible…minute. It seems like we do this song and dance every year, but this year in particular, we had a few circumstances that held us back from filing earlier…not that we started them early or anything.
James left for a business trip the morning of Wednesday, April 3 and returned Saturday, April 6. I planned to use this opportunity to start and finish our taxes and have them ready to go over together by the time he came back home. Unfortunately, I got a little overwhelmed with all of our properties, dozens of receipts from Home Depot, and miscellaneous expenses from forgotten renovations, and I didn’t quite get as far as I wanted.
While we (I mean James) had most of our real estate affairs recorded and organized, I still had to log onto all of our mortgage and insurance accounts, which was time-consuming to do that for every property we own. I also kept having to look at both of our email accounts for invoices, closing statements, and various other housing documents.
Since the weather was nice on Sunday, James wanted to start getting one of our duplexes ready for an exterior paint, so that took a little time away from my tax work. But eventually, I got as far as I could on my own on the taxes the following Monday. However, James and I didn’t actually sit down to go over everything until the following Saturday evening, after a long day of getting a washer & dryer and painting all afternoon until dark. It lead to a lot frustration because we couldn’t submit our state tax via web, but it also lead to a great return after James finished combing through everything and finding things that I missed or forgot to enter.
Before James got his hands on the taxes, we owed about $1300. After he worked his magic and found receipts and invoices from forgotten expenses, we found ourselves with a whopping $9 refund. Some things that I completely forgot about, but James remembered include a new water heater for a duplex unit, another water heater and bathroom repair at our condo from a water leak, and a roof replacement at a duplex. These totaled close to $4,500, so that would have been an expensive mistake to have forgotten about.
Since our state tax gave us an error for web submission, we had to mail in our return. This lead to another whirlwind. When I got off work, James told me he forgot to send off our state return and asked if I could take it by the post office. In order to be considered on time, the letter had to be post marked on 4/15. I tried going by the UPS store, a dry cleaner store disguised as USPS but was only a drop box, and finally a USPS store that was open later. Unfortunately, EVERYONE else decided to wait until the last possible minute to go to the USPS store and send their state return via mail because the post office was the busiest I had ever seen it. Luckily, I made it right before closing and a kind USPS worker took mine and another lady’s letters so she could be post marked for 4/15. God bless those postal workers because they must have been working their asses off all day.
This whole thing has been one big learning experience. I keep telling myself that I refuse to do the taxes myself next year and the following years. It is also a shocking reminder to keep better track of our expenses from repairs to renovations and other things needed for next year’s taxes. As I was typing this out, I remembered a $1000 expense from the roof repair that we completely forgot to add, and somehow slipped through the mountain of receipts and pages of spreadsheets we have. However, because we waited so late to do them, it’s too late to go back and add that expense.
Life is all about making mistakes and learning from them. I have learned not to put off doing our taxes so late next year. We can’t afford to leave out large purchases for our properties, and we can’t wait until last-minute because there is always going to be something more time-consuming or more pressing that might have to get put on the back burner for a few days. So tell me, do you do your own taxes or do you have a professional do them? Are you a procrastinator like us or did you submit your taxes early?


  • Tracey

    We hire someone to do our taxes. I remember doing my taxes when I was single and 19 and being stressed out with only a couple W2 jobs. I cannot imagine doing them now with my husband’s business, my W2 and two investment properties. I now have the stress of having to find a new tax person! After doing our taxes for over 20 years, my faithful and VERY affordable tax professional is retiring. I will start looking for that person NOW because I am not a procrastinator. Waiting to the last minute on anything stresses me out, so I try to stay ahead of the game.

    • Emily Lowery

      Yes it stressful with W2 jobs and multiple investment properties, and we should have hired someone but hindsight is always 20/20.
      That’s always hard having to find to find a new person you trust. Hopefully you can find someone great! We need to start looking now for a tax professional as well so we can take full advantage of tax benefits and not having to do them ourselves. I know that I get stressed waiting until the last minute on things, but it still ends up happening!

  • Laura

    You have a few options that you can use for 2018 taxes and beyond. If you know you are due a refund, April 15 is just a suggestion—there is no penalty for filing late other than the IRS hangs onto your money longer. If you owe, you can also file an extension for extra time but you’ll have to estimate your taxes and pay them before 4/15 or you’ll be late and have to pay a penalty. For the expense you forgot, you can do an amendment to your taxes and refile. That’ll get you a little more money back.

    • Emily Lowery

      This is great information, thank you Laura! I didn’t realize you could do an amendment on your taxes, so we’ll definitely be doing that.

    • James

      As much as we bitch, we prefer to do our own taxes too. It can just get overwhelming pretty quick if you aren’t as organized as you should be….which we could be much better at our organization. We have been doing better at keeping things more organized this year after we had such a headache with our taxes. We will see how it goes in April 2020, haha!

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