3.8% medicare surtax on investment properties

The Wall Street Journal tries to sort out the question of what particular transactions the new medicare surtax will apply to. 

In general, someone with a day job who collects rents on the side must include that income (net of expenses) in investment income, potentially subjecting it to the surtax, while someone whose sole occupation involves owning and operating real estate typically would not be subject to the tax. In either case, any profits from a sale could get hit with the surtax.

If you're planning to sell rental real estate or other investment property, run, don't walk, to a trusted tax expert.

Read the entire article.  It will not provide definitive answers, but it does identify the issues.