Many years ago, I purchased an equity membership in a golf club. Along the way I also paid an assessment to finance the construction of a new clubhouse. Now, I would like to leave the club, but the sales list is far too long. Just “walking away” is not an option. However, for a relatively nominal fee, the club will allow me to convert my current equity membership into a non-equity membership. This would allow me to just “walk away” after one year if I choose with no penalties. Of course, I forfeit my “equity” in the club. Seems to me, I am effectively selling my equity membership back to the club for $0 and purchasing a non-equity membership for $x. Can my original purchase amount and/or assessment (for new clubhouse) be considered a capital or personal loss for tax purposes?