Chicago → Puerto Rico: Remote Flip Roadmap

A working plan for moving the fix-and-flip business to a remote model (~2 years out). Check the tasks off — your progress saves on this device.

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The shift GC vs crews Flip vs BRRRR Stage playbook Team Tax flag Runway Tools

The shift: you become the brain, not the hands

Today you are the eyes and hands — you walk every property with the Scope Sheet and manage the subs on site. From Puerto Rico your job narrows to four things you can do from anywhere: capital, underwriting, deal flow, and systems. Everything physical becomes a hire.

The whole challenge in one sentence: the two roles you do best — walking the house and running the rehab — are exactly the two that go remote-hardest. Solve those two and the model works.

Time zone isn't a real obstacle — PR is Atlantic Standard (no daylight saving), one hour ahead of Chicago most of the year, two in summer.

GC vs. multiple trade crews

Short answer: stay with trade crews while you're in Chicago; for the remote phase, trade crews run by a local PM you've groomed — and if you can't build that person, use a GC or lean into BRRRR.

	General Contractor	Trade crews (you/PM)
Cost	Markup 15–25% — $24k–$40k on a $160k rehab	Lean — that markup is your margin
Coordinates	The GC: schedule, permits, problems	You or your PM: every trade & handoff
Remote difficulty	One relationship — remote-friendly	6–8 trades across 2,000 mi — brutal solo
Control	GC's subs & standards	Your subs, finishes, pricing
Risk	Honest GCs are rare; corner-cutting	Theft/ghost-subs with no one watching

The only reason you build lean is that you do the GC's job for free — and you can't from the beach. Use the helper:

Do you have — or can you build in the next two years — a trusted on-ground PM?

→ Trade crews + your PM. Keep your margin edge. Pay the PM a salary, per-job fee, or small % to be your on-ground self. This is the target model — it lives or dies on trusting that one person, so vet them in person before you leave.

→ Use a GC, or shift toward BRRRR. Accept the $25k–$40k/deal markup for one remote-manageable relationship — works only if your spreads are fat. Or weight your book toward BRRRR, which tolerates a GC far better than a flip does (see next section). Spend the runway trying to develop that PM; it changes the whole economics.

Permit note either way: in Chicago, electrical and plumbing permits can only be pulled by licensed contractors — your licensed subs pull their own, or the GC pulls the general building permit.

Flip vs. BRRRR once you're remote

Lean toward BRRRR as the move nears. A flip is a race with intense on-site management — hardest from PR. A BRRRR you rehab once, refinance, then a property manager runs it and you collect cash flow from anywhere.

A GC's markup hurts a flip far more than a hold: on a flip it comes straight off a thin one-time profit; on a BRRRR it just slightly raises your basis — you refi against ARV, recover most of your capital, and it cash-flows for years.

Your buy box already computes both. In PR, weight the BRRRR column more heavily in which deals you chase. Keep flipping the fattest spreads; BRRRR the rest.

Stage-by-stage remote playbook

The paperwork, money and decisions travel; the eyes, hands and physical access don't.

Stage	You, from PR	Local hire
Find	InvestorLift, MLS, nightly screener	—
Analyze	Scope Sheet + comps (if you trust the condition data)	Scout to walk + photo it
Offer & buy	Write offers, negotiate, e-sign	Attorney + title (required in IL)
Finance	Manage hard money + HELOC	CPA (PR + mainland)
Renovate	Scope, draws, materials, bid packets	GC or PM + licensed trades
Sell	List on MLS, market, negotiate	Showing access + photographer

Your standing team — build before you leave

Non-negotiable:

Real estate attorney — IL is an attorney-close state, both buy and sell.
Title / escrow company.
CPA who knows PR and mainland tax — you're a dealer on flips.
Licensed electrician + plumber — only they can pull those permits in Chicago.
Builder's-risk / vacant-property insurance — a vacant job that burns or gets stripped can wipe out the deal.

What makes remote work:

GC or on-ground PM — the make-or-break hire. Groom this person now.
Local scout — walks properties, shoots the photos/video you scope from.
Showing access — a showing service or local agent partner lets your listings be seen while you hold the license from PR. A showing service sends a local licensed agent to open the door and run a showing for a flat fee (~$30–$50 each), no commission.

Tax flag: don't assume Act 60 covers Chicago income

People move for Act 60's ~0% tax on PR-sourced gains. But income from Chicago real estate is US-mainland-sourced — Act 60 generally does not shelter it. Your flip profits would still be taxed federally as dealer income + SE tax (the ~38% the Scope Sheet models), even as a PR resident.

Not tax advice. One action item: before you build PR tax savings into the plan, pay a PR + mainland tax attorney to tell you exactly what qualifies.

The two-year runway

The next two years are when you build what remote requires — you can't vet a GC or sub from PR cold. Tap a task to check it off.

How the tools carry it

Scope Sheet + live comps — underwrite any deal from anywhere. Validated against Leamington within 16%.
Photo/vision scoping (item 8) — becomes core. A scout uploads photos; the vision pass pre-flags condition; you confirm from PR.
Bid packets (item 9) — one scope → trade-by-trade bid requests.
Nightly screener (item 10) — runs your InvestorLift feed overnight and flags what clears.
Reno/project tracker — your Leamington workbook, systematized: draws, actuals, progress.

Build priority for the move: item 8 first (remote scoping is the hardest gap), then the screener and tracker.

Editable master copy lives as a Claude doc; this hub page mirrors it and tracks your task progress locally. · Last updated 2026-10-23.