Options, Tax and Concentrated Positions!!

Hedging a concentrated position with options sounds simple, until US tax rules turn it into a minefield. Someone said it was “too hard”, but over a few days, with help from Claude Code, I built a proof-of-concept tool for managing concentrated positions.
What it does:
– Flags tax surprises in real time as you model options
What it lets you do:
– Choose and visualize your volatility surface
– Set up current holdings with embedded gains/losses
– Create, compare, and optimize multiple option and structured-product packages (PVF)
– Filter forecast simulations down to the scenarios that matter for you
– Set after-tax goals
Where it could go next (from proof of concept to real model):
– Multiple assets, currently limited to AAPL as the concentrated position and SPX as a stand-in basket for other holdings and tax-loss harvesting
– Multiple time periods, currently defaults to 1 year for data simplicity and easy comparison