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June 14, 2014 6:25 PM Subscribe
I'm having trouble keeping my finances organized for tax purposes. Special considerations: renting out a property, medical expenses.
posted by unannihilated to Work & Money (5 answers total) 2 users marked this as a favorite
My situation is pretty simple. I rent out one residential property, a house, and as far as my medical expenses go most of them are covered by insurance. So I didn't think this would be complicated, but it is. In both cases, I have many small expenses that add up to a not insignificant amount. The information is currently spread everywhere because I use so many methods of payment. I use several credit cards, a debit card, direct deposit/deduction, checks, and cash. As far as the property expenses go, some of this can't be avoided. My handyman isn't going to start taking credit cards. I can't pay the hardware store the two bucks for a key duplication in anything but cash. The water company doesn't do online bill pay. My credit cards gives reward points, so I want to use them for most house-related purchases, but then Costco will only take a debit card. Etc.
My receipts are spread everywhere too. Some are in my wallet, some I stuck in a file folder, sometimes I bought personal stuff at the same time and left them in the bag because I thought I might return that shirt. Some I never got because there weren't any or I didn't realize they were important. Some I can't find now. Etc.
This is all true for the medical expenses as well: Sometimes I'm paying co-pays at the point of service with a card, other times I'm getting bills later in the mail that I pay with a check because setting up online bill payment for the lab fee turned out to be really arduous and I only get labs once a year anyway or the doctor's office charges a fee if I want to pay on the phone with a card. Etc.
Another part of the problem is that I didn't always realize something was important for tax purposes until later. Oh, those trips count as a business expense? Well, let me see if I can remember what method of transport I used and how I paid for it and how much would the tolls have been? Etc.
So, help. How do I track this stuff so come tax time I can pull out the numbers my accountant needs quickly and easily as well as get all the deductions I should? I had to file an extension for last year's taxes, so I'm still working on gathering everything together from last year and want to do better for next year. I'm feeling overwhelmed by this, and more importantly, I know I'm losing money I can't afford to lose by not being on top of it.