Reader Mark asked in Reset Cost Basis Higher By Realizing Capital Gains: I live in NYC where home prices seemingly always on the rise. When I reach the 250k threshold of tax free capital gains, should I think about selling and re-buying something [...]
Adjust Cost Basis for ESPP Sale In H&R Block Software
The new IRS regulation for ESPP shares acquired in 2014 or thereafter requires adjusting the basis. Otherwise you will be double-taxed on the discount. Reader Roger asked me how to do it in H&R Block software. If you use TurboTax or H&R [...]
Adjust Cost Basis for ESPP Sale In TurboTax
Several readers asked me how to do taxes on ESPP sales in my article about doing taxes on sales from vested RSUs: Restricted Stock Units (RSU) and TurboTax: Net Issuance. It's similar but not exactly the same. The new IRS regulation for shares [...]
Change Your Cost Basis Method From Average Cost To Specific Identification
If you have a "regular" taxable investment account (anything other than your tax advantaged accounts such as your 401k, 403b, IRA, Roth etc.), you should understand the different cost basis tracking methods and how they affect your taxes when you [...]
Reset Cost Basis Higher By Realizing Capital Gains
I updated this article I first wrote two years ago. It's still relevant today since Congress made the 0% tax rate on long term capital gains permanent in early 2013. 2013 is coming to an end. It's been a great year for the stock market. For those [...]
Converting to Roth and Harvesting Capital Gains Under Obamacare ACA Premium Subsidy
I posted this chart in the previous post Stay Off Obamacare Premium Subsidy Cliff. It looked at the sudden jump in the net health insurance premium once your income goes above the premium subsidy cliff set at 400% FPL. This time we zoom in and [...]
Happy Trails With Income Poor
This is the third and final installment on my Asset Rich Income Poor strategy. The road to asset rich sounds simple at a high level but it's not that easy at the details level, because every decision you make has tradeoffs. The tradeoffs affect the [...]
Fiscal Cliff Deal and Dividends and Capital Gains
Today we look at how dividends and capital gains will be taxed after the fiscal cliff deal, officially known as the American Taxpayer Relief Act of 2012. Don't be surprised it gets a little more complicated. First of all when I say dividends and [...]
Obamacare 3.8% Medicare Tax and Alternative Minimum Tax (AMT)
Now that the health care reform law is upheld by the Supreme Court, the 3.8% Medicare tax on unearned income for high earners is also here to stay. It will come into effect in 2013. Just to recap, the chart below shows how it works: The tax is on [...]
