I’m researching a potential move to Puerto Rico under Puerto Rico Act 60 Chapter 2 (resident investor decree) and wanted feedback from people familiar with the tax side of active options and/or crypto trading.

My understanding is that Chapter 2 is not limited strictly to passive long-term investing. Puerto Rico tax law broadly defines capital gains and specifically treats certain gains/losses from options activity as short-term capital gains or losses.

My situation:

• Planning to apply for a Chapter 2 decree before end of 2026
• Move to PR around 1/1/2027 and become a bona fide resident under IRC §937
• Spend the large majority of my time in Puerto Rico (~300 days/year)
• Rent initially, then buy a primary residence in PR
• PR driver’s license, voter registration, bank accounts, etc.
• No meaningful center of life outside Puerto Rico after relocating

Trading structure:

• Personal brokerage account only (under my SSN)
• Separate/new brokerage account funded with already-taxed mainland cash after relocation
• No pre-move investments/gains realized after moving
• No outside investors or customers
• No LLC/corporation for trading
• No §475(f) mark-to-market election

Trading style:

• Mostly defined-risk options strategies:
  • iron condors
  • debit spreads
  • collars
• Usually held 1–2 weeks, occasionally longer

My understanding is:

• Under IRS Topic 429, a trader without a §475 election can still retain capital-gain treatment
• IRC §1234 generally treats options gains/losses as capital gains
• Under IRC §865, gains from sale of personal property are generally sourced to the taxpayer’s tax home
• If I become a bona fide PR resident and generate gains after relocation, those gains may become Puerto Rico-source income
• Under IRC §933, Puerto Rico-source income of bona fide residents is generally excluded from U.S. federal tax

So the theory is NOT:
“short-term gains magically become tax free”

But rather:

• short-term options gains still retain capital-gain character,
• they become Puerto Rico-source after establishing residency,
• and Chapter 2 potentially applies to qualifying post-move gains.

I also understand U.S.-source dividends/interest may still be federally taxable, and I’m not trying to claim otherwise.

I’m also not trying to force this into an export-services/business-income theory — the activity would simply be personal proprietary trading using my own capital.

Main question:
Has anyone here successfully structured active personal options trading this way under Chapter 2? And has anyone seen the IRS argue that short-term options trading without §475 somehow becomes ordinary income solely because the activity is frequent/business-like?

Appreciate any insight from people who have dealt with this directly.