STR with Leslie

Start here if you're buying

Find the STR that's actually worth buying.

Buying an STR is a strange combination of real estate, business, hospitality and emotion — and it's incredibly easy to become convinced a property works because you already want it to.

Aerial view of a beach community with rental homes, pools and beach access

The seven questions I'd want answered first.

  1. 1.

    Can I actually operate the STR I intend to run here?

    Rules, restrictions, licensing, HOA and what the property is genuinely allowed to be.

  2. 2.

    Is this property objectively worth pursuing?

    Location, guest demand and how it compares to what guests could book instead.

  3. 3.

    Am I buying the opportunity — or buying what I personally love?

    Separating the premium you're paying from the premium guests will pay.

  4. 4.

    Do the numbers actually support the property?

    The assumptions underneath the spreadsheet, not just the totals in it.

  5. 5.

    What am I really buying, and what will it take to get guest-ready?

    Condition, furnishings, systems and the real cost between closing and first booking.

  6. 6.

    Do I have the right people and the right answers around the decision?

    Who you're relying on, and what nobody has actually answered yet.

  7. 7.

    What does everything I know actually support me doing next?

    Turning a pile of information into a clear next step.

Know Before You Offer masterclass and printed Property Evaluation Workbook

Want the framework? Start here.

Know Before You Offer

  • A self-guided framework you work at your own pace.
  • Applied to one real property, start to finish.
  • The masterclass plus the Property Evaluation Workbook.
  • Better questions and clearer assumptions before you make an offer.

$37 one-time

Get Know Before You Offer

No investment grades. No fake certainty. No formula telling you whether to buy. Just a much better way to understand what your decision is actually resting on.

Want my eyes on the property too?

Bring me the property.

  1. 1 — You send it over. The listing, your numbers, your intended strategy and whatever information you've collected so far.
  2. 2 — I review it before we meet. So the call isn't spent catching me up.
  3. 3 — A 60-minute private property strategy session. Strengths, assumptions, economics and the questions still unresolved.
  4. 4 — A concise written follow-up. So you keep the thinking after the call ends.

$497 founding client rate

Bring me the property

Education and strategy only — not legal, financial or investment advice, and not a recommendation to buy any property.

Resort-style pool steps from the Gulf beach

Already own one instead? Marketing and optimization live over here.

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