The structure of these tax laws have too many definitional problems at the outset: (i) what is real v. personal property; (ii) when do you rent an asset verses use it in running your trade or business; (iii) how much of your physical effort is required to earn a buck (SECA or NIIT); and (iv) when are you special enough to take losses (i.e., passive, active, materially participating or something else altogether).

Presented with a similar dilemma, it took these guys only four minutes to reach a well-reasoned conclusion.  If only Congress could do that.  She's a witch! (youtube.com)