This can backfire badly - I tried the property management route and ended up with terrible tenants who trashed the place. The 10% fee the management company took hardly seemed worth it considering all the headaches. Sometimes a clean break is better financially and mentally.

Do you have to notify your brokerage which specific shares you want to sell before the sale, or can you do it afterward when filing taxes?

You need to specify which shares you want to sell at the time of the sale - you can't decide later when filing taxes. Most online brokerages have an option during the sell process where you can choose "Specific Identification" instead of FIFO (First In, First Out) or average cost. When you choose specific identification, you'll be able to select the exact lots (shares purchased on specific dates at specific prices) that you want to sell. This gives you maximum control over the tax implications of your sales and is essential for an effective homegrown dividend strategy.

For Roth IRAs, the withdrawal rules are a bit different. You can always withdraw your contributions (principal) tax and penalty free at any time. It's actually even simpler than with taxable accounts because you don't need to worry about specific identification of lots. The IRS considers withdrawals from Roth IRAs to come from contributions first, then conversions, then earnings. So you can just keep track of your total contributions over the years, and as long as your withdrawals don't exceed that amount, they're completely tax-free.

Is it worth paying for the deluxe or premium versions of these tax programs? I always use the free versions but wonder if the paid ones catch more deductions?

For most simple tax situations, the free versions are perfectly adequate. The paid versions add value mainly if you have more complex situations like self-employment income, rental properties, investments, or itemized deductions. The other benefit of paid versions is better support options - some offer tax pro review or the ability to chat with a tax expert if you get stuck. But if you just have W-2 income and take the standard deduction, you're generally fine with free versions. Just make sure you're using the actual free version and not getting upsold on features you don't need.

Second this! Been using FreeTaxUSA for 3 years now. When I switched from TurboTax I actually got a BIGGER refund with FreeTaxUSA because it found an education credit TurboTax missed. Plus they don't constantly try to upsell you on stuff.

Thanks for the validation! I was worried I'd missed something since it was so much cheaper. Good to know about the education credit too - I'll have to double-check that section since I'm taking some community college classes.

Thanks for the Free File link! Do you know if they handle state taxes too or just federal? I always get confused about which services include both.

Some of the Free File partners include free state returns, but not all of them. When you go to the IRS Free File site, you can see which providers offer free state filing along with federal. It varies by state too - some states have their own free filing programs separate from the federal Free File program. I'd recommend checking the specific provider details when the program opens in January. The IRS usually has a tool that helps you find which Free File option is best for your situation, and it will show whether state filing is included or not.

Great idea with the calendar reminders! Does anyone know if there's some kind of email alert system from the IRS where they notify you when filing season begins?

Does this mean I should be withholding more than 10% from my current unemployment checks? The system only gives me option for 10% or nothing, no way to withhold 22% or whatever my actual bracket is.

You're right that the unemployment system typically only allows for the 10% withholding option, which is frustrating. Since you can't increase the withholding percentage through the unemployment system, you have two main options: You can set aside additional money yourself with each unemployment payment - essentially creating your own additional withholding. For someone in the 22% bracket, you might want to save an extra 12% of each payment. Alternatively, you can make quarterly estimated tax payments to the IRS using Form 1040-ES. This allows you to send in additional tax payments throughout the year to cover the gap between the 10% being withheld and what you'll actually owe.

I use the tax calculator on smartasset.com instead. It lets you input both regular income and unemployment separately and gives a pretty accurate estimate of what you'll actually owe. Way better than the IRS one for people with mixed income sources.