My Puerto Rico buy box
The exact criteria I use to filter properties worth analyzing from the ones that waste your time.
A step-by-step program for finding, analyzing, financing, launching and operating short-term rentals on the island. Built on what works in Puerto Rico, not generic mainland advice, so you invest without guessing, overpaying or making costly rookie mistakes.
Short-term rentals in Puerto Rico can be extraordinary. People rarely lose money because the market is bad. They lose it because they walked in blind.
Most people can't get an agent to reply when they find a property they want to see. The good deals are gone before they get a foot in the door. I see houses quickly.
Without local comps and a real buy box, off-island buyers routinely pay top dollar and erase the cash flow before they get the keys. I negotiate.
Half-finished renovations, blown budgets and disappearing crews. On an island where relationships are everything, the wrong vendor can cost you a season. I vet my contractors.
Mainland lenders get nervous and local rules confuse them, so they assume they need all cash. The deal dies, or they drain every dollar of liquidity. I have multiple lenders.
STR registration, municipal rules and compliance trip up new operators constantly. Get it wrong and a listing can vanish overnight. We get permits expedited.
Utilities, logistics, hurricane prep, seasonality and off-island management. The things nobody warns you about until they cost you money. We are connected.
Every one of these mistakes is avoidable. The investors who win aren't smarter or richer. They had the map before they started walking.

For 7 years I built my career in finance, at State Street Bank and later J.P. Morgan, managing and analyzing large amounts of money.
On paper, it was a great career. But every quarter I'd look at the numbers and realize I was helping build wealth for other people, not creating financial freedom for myself. So I left the corporate world and bet on myself.
I moved into real estate investing and found my passion helping people invest in short-term rentals here in Puerto Rico. I didn't get everything right. I learned the hard way.
"I underestimated renovation costs. I struggled sourcing materials. I showered with gallons of water when the water went out and slept in the heat when the power went out. I heard 'no' from lenders more times than I can count. I almost lost it all."
Those mistakes weren't cheap, but they became my greatest education. Today I'm an Airbnb Superhost. I've helped develop and manage short-term rentals across Puerto Rico's eastern region, and guided investors from all over the U.S. through buying, renovating and operating vacation rentals on the island.
As more people asked me the same questions, I realized I could save others years of trial and error by teaching the system I wish I'd had. That's why I created this program.
This isn't about convincing you I'm perfect. It's about showing you I've already walked the path you're trying to take. You're the one building your future. My role is to be your guide: give you the roadmap, introduce you to the right people, and help you move forward with a strategy tested through real experience.
Properties, guests, investors and the weekly work of running rentals in Puerto Rico.
A U.S. jurisdiction with a passport-stamp feel: no currency exchange and no passport for U.S. travelers. In 2024, its visitor economy set a record.
Record visitor spending in 2024, and no passport needed for U.S. travelers. A deep, steady demand pool for well-run rentals.
Beaches, mountains, rainforest and culture. An asset in a place people dream about visiting, and revisiting.
Incentive programs have drawn investors to the island. Eligibility and conditions apply, and we cover what to ask your CPA.
Tourism is the island's third-largest private-sector employer. A market that rewards professional operators.
Source: 2024 Economic Impact of Tourism in Puerto Rico, Tourism Economics for Discover Puerto Rico. Calendar year 2024.
Important: tax incentives carry specific eligibility rules and obligations, and market conditions change. Inside the program we teach you the right questions to bring to a qualified Puerto Rico CPA and attorney. We don't give individualized tax or legal advice.
Every step builds on the last. Open any step to see what's inside.
The tools, templates and live support that compress years of trial and error into a clear, repeatable process.
Everything you need to purchase a property in Puerto Rico under one proven program.
The exact criteria I use to filter properties worth analyzing from the ones that waste your time.
How to vet, scope and manage crews on the island so renovations finish on time and on budget.
Real Puerto Rico deals underwritten end to end, so you copy the thinking, not just the formula.
We help you build and optimize your listing, pricing and account settings so your property launches ready to book.
The step-by-step list that takes a property from closed to live and booking, with nothing forgotten.
Qualified properties get our team's full-service hosting and management at an exclusive members' rate.
Outcomes from investors Roberto has worked with on the island. Individual results, not typical or promised outcomes.
Before
After
The buyers
Villa Verde
Property
Closing
Victor, right
Owner's earnings
Guest reviewFigures reflect specific properties and individual results. They are not typical results or a promise of yours. Your outcome depends on the property, market, financing and your own effort.
"We were tired of how expensive real estate was in New York until Roberto showed us new opportunities that generate real cash flow for us."
"I spent so much time thinking about buying in Puerto Rico because of fear, but Roberto gave me the confidence I needed to buy my first investment."
"Just speaking to Roberto saved me months of lost time trying to figure out real estate in Puerto Rico on my own. I have no regrets."
"Roberto went from being a friend to a brother. He helped me accomplish my goal of owning a piece of Puerto Rico for my family."
"If you want to avoid all the mistakes most of us make, hire a mentor like Roberto. If not, keep watching YouTube videos and learn the hard way like everyone else."
Realtors, lenders, property managers, designers, land experts and investors who share exactly how they do it. Members get every live session and the replays.
Local realtorFinding off-market deals across the eastern region.
Property managerRunning a rental from off the island: guests, cleaning and maintenance.
Interior designerDesigning spaces that photograph well and command higher rates.
Land expertBuying land in Puerto Rico: titles, access, utilities and zoning to check first.
Loan officerFinancing Puerto Rico deals, including DSCR and second-home loans.
Portfolio investorScaling from one property to a full portfolio on the island.
New guests join throughout the year.
I don't just teach this. I do it. Real numbers from properties I operate, so you can see the model working before you join.


After
Guest rating: weighted average of Villa Vista (4.85, 71 reviews), Villa Verde (4.82, 34) and Villa Brisa Serena (4.93, 44) on Airbnb, as of September 30, 2026. Figures reflect specific properties and are shared for transparency. They are not a promise of your results.
A stripped-down version of the deal analyzer inside the program. Move the sliders. Occupancy is the number people usually get wrong, and it can turn a good-looking deal upside down.
Simplified on purpose. The real analyzer adds seasonality, cleaning turnover, storm-season vacancy, financing structure and taxes. Illustration only, not a projection.
Run your real numbers with usThe questions running through your head right now, answered straight.
You can learn pieces for free. The problem isn't access to information. It's sequence, context and the cost of being wrong. YouTube gives you disconnected tactics from markets that aren't Puerto Rico. This gives you one order of operations for this island, plus a person to ask when a real deal is on the line.
Then Step 1 is built for you. It assumes zero experience and walks you from fundamentals to your first acquisition. Beginners have no bad habits to unlearn, and follow the system instead of improvising.
Many Puerto Rico operators live off the island, and so do many of our students. We teach remote acquisition, vetting vendors from afar and managing without being there. Distance is a logistics problem, and logistics have a playbook.
Before you invest in real estate, invest in understanding every funding option: HELOCs, eligible 401(k) and self-directed IRA funds, selling underperforming assets, private capital, partnerships and creative financing. The skill of funding deals is worth more than the cash itself.
The program is self-paced, and the operations side is built on automation, SOPs and systems so it doesn't consume your life. The goal is to buy back your time, not trade more of it.
Markets always change, which is why you want a framework instead of a hot tip. We teach you to read demand, underwrite conservatively and adjust as conditions shift. Operators who understand the fundamentals adapt.
Everyone is welcome in the free community. The Accelerator is for people ready to plan a purchase.
Everyone starts in the same place. The readiness check decides whether a strategy call makes sense now or later.
Five questions about your experience, capital, timeline and goals.
2 minutes · no paymentIt appears as soon as you finish: a strategy call with Roberto, or the free community for now.
InstantWe talk through your goals and situation, answer your questions, and decide together whether the program fits. Pricing is shared on the call.
30 minutesAnything else, ask inside the free community or on your strategy call.
No. Many successful operators, and many of our students, run their properties from the mainland. We teach the remote acquisition, vendor-vetting and management systems that make it work.
Not at all. Step 1 assumes zero experience and builds from the ground up. Complete beginners often progress fastest because they follow the system instead of improvising.
It varies by deal and financing strategy. We dedicate the strategy call to understanding where you are financially, so we can build a budget or game plan for your next purchase.
Free content gives scattered tactics from many markets. This gives one sequence built specifically for Puerto Rico, plus tools and live support when a real deal is on the line.
Most agents have little or no investment experience. We actively invest on the island and understand the ins and outs of investing here. We aren't here to show you kitchens and bathrooms. We're here to show you ROI and cap rates.
It's self-paced. Many students move through the core material in a few weeks of focused effort, then keep using the tools and coaching as they execute.
The focus is short-term rentals in Puerto Rico, though much of the acquisition and financing material applies to long-term rentals too. Some clients want an investment; others want to move to the island and don't know how.
We reference industry tools like AirDNA, PriceLabs and Hospitable and show you how to use them. Third-party subscriptions are separate and optional where noted.
No, and be cautious of anyone who does. We provide education, systems and support. Your results depend on your market, deal, financing and effort. We help you take more calculated risks and feel more confident in your deal.
We include emergency and hurricane preparedness planning so you can protect guests, your property and your reviews. It's a core part of operating responsibly on the island.
We teach the landscape and the right questions to bring to a qualified Puerto Rico CPA and attorney. We don't provide individualized tax or legal advice, but we can point you in the right direction.
Live weekly group Zoom calls where you bring your deals and questions and get real-time guidance. Replays are available to members if you can't attend live.
Yes. A private community of investors and operators, on and off the island, so you're never figuring things out alone.
Step 2 is built to prevent that, using real data and a defined buy box so you target high-demand areas, not just pretty listings.
Yes. The program is self-paced, and the operations side is designed around automation and SOPs so it fits around a full-time career.
We teach financing strategies and provide templates and scripts. We are an education provider, not a lender, broker or financial advisor. We do connect you with lenders in Puerto Rico who can work with you on pre-approvals.
You take the two-minute readiness check and see your next step right away. If it's a fit, you book a strategy call where we talk through your goals, answer your questions and decide together whether the program is right for you. No pressure.
The content is maintained, and the live coaching keeps you current as the market, tools and regulations change.
Absolutely. Local knowledge is an advantage, and this program helps you turn it into a professional, repeatable investing process.
Yes. Despite what you may see or hear online, there will always be opportunities for anyone to invest in a piece of the island. All backgrounds are welcome, and encouraged to give back to our local communities.
You've seen the opportunity and the roadmap. You have a guide who has already made the mistakes, the tools to skip the guesswork, and a community walking the same path. The only thing left is the decision.