JACK COSTIGAN / NASHVILLE STR ADVISORY
For investors committing meaningful capital to a short-term rental, the details matter. Jack Costigan brings Nashville market knowledge, transaction experience and a disciplined property review to the decision.
WHY THIS PRACTICE EXISTS
A short-term rental purchase brings together a real estate transaction, an operating business and a set of local rules. The advice needs to connect all three.
That is the gap Jack built his STR advisory practice to address. Investors can find photos, asking prices and revenue estimates almost anywhere. The harder work is understanding how the property is allowed to operate, how dependable its income assumptions are, what it will cost to own and how those pieces fit the investor’s goals.
As founder of The Costigan Group at Compass and founder and lead of Compass’s Short-Term Rental Division, Jack works with buyers and sellers who want that level of detail. His Nashville practice covers non-owner-occupied STR acquisitions, furnished rental properties, operating records, property positioning and the planning required for a sale.
His completed transactions include downtown investment condos, rooftop rentals, neighborhood properties and destination-oriented rentals outside the city. Working on both sides of these sales informs the questions he brings to the next acquisition: what buyers need to see, what owners need to prepare and which unresolved details can complicate a closing.
WHO JACK WORKS WITH
Jack advises high-net-worth clients, experienced property investors and buyers entering the STR market for the first time. The brief may be a single acquisition, an addition to an existing portfolio or the sale of a property that has been operating for years.
For clients investing from another state, the value is in having someone local who can connect the analysis with what is happening at the property. For experienced investors, it is having an advisor prepared to discuss the assumptions behind the asking price and the work required after closing.
The relationship starts with your capital, financing, time horizon and appetite for operating involvement. Those choices shape the search, the questions asked of a seller and the opportunities worth pursuing. A property can be attractive and still be the wrong fit for your plan.
Talk through your investment briefWHAT DETAILED ADVISORY LOOKS LIKE
A strong review makes assumptions visible. These are the areas Jack works through with clients, drawing on property records, seller documentation and the appropriate local professionals.
Start with the specific parcel, zoning, permit record, association documents and ownership structure. Identify what must be confirmed, by whom and before which contract deadline. An STR reference in a listing is the beginning of that work.
Review the period covered by the seller’s numbers, monthly seasonality, owner use, refunds and future reservations. Compare platform records with the operating statements provided. Separate what the property has earned from what a new owner hopes to earn.
Account for management, cleaning arrangements, utilities, insurance, taxes, supplies, maintenance and replacement reserves. Understand which expenses are missing from a seller’s summary and which costs will change under your ownership.
Study bedroom and bathroom configurations, parking, gathering spaces, noise exposure, amenities and access to demand drivers. Compare the property with rentals competing for the same guest, then consider the cost of furnishing or repositioning it.
Include financing costs, immediate repairs, furnishing, setup and an operating reserve in the acquisition plan. Pressure-test a slower opening or lower-revenue period, so the purchase decision reflects more than a down payment and an optimistic calendar.
Consider the next buyer before becoming the owner. Property condition, operating records, association restrictions, financing options and the ability to support the intended use can all shape the future resale audience.
FROM INFORMATION TO A DECISION
The point of a detailed process is a clearer decision. Jack helps organize the property’s strengths, the assumptions behind its performance and the questions that need an answer before you commit.
That can mean revisiting the price, budgeting for a different operating plan, asking for additional records or deciding to keep looking. The recommendation should follow the evidence and your objectives.
Bring the available permit information, association records and seller materials into the same conversation.
Discuss the difference between gross revenue, recurring costs, capital needs and financing.
Keep inspections, lender requirements, documentation and contract deadlines connected.
Work through furnishings, access, management and reservations before possession.
COMPLEX TRANSACTIONS NEED COORDINATION
Some Nashville STR opportunities involve an entity sale or a membership interest purchase agreement, often called a MIPA. The ownership structure, permit history, contracts and proposed transfer deserve their own review. Jack helps coordinate the real estate side of that process with the client’s attorney, lender, tax advisor and other relevant professionals.
The same discipline applies to a more conventional purchase. Who holds the permit, what the association allows, what the lender will finance and what a management or booking platform will permit are separate questions. A credible plan identifies the answers and the remaining dependencies before they become closing-day surprises.
Explore Nashville STR regulationsJACK’S STR TRACK RECORD
Rooftop rentals, investment condos and destination properties. A selection from Jack’s broader STR transaction history, with sale prices, property details and buyer or seller representation.
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Showing 6 of 23 featured transactions
Selected past transactions, not current listings or a complete career sales record. Buyer and seller labels describe Jack’s representation. Historical STR use does not establish a future buyer’s permit eligibility.
FOR OWNERS PREPARING TO SELL
Selling an STR requires explaining the property and its operation. Jack helps owners organize performance records, document what is included and present the spaces and amenities that compete for bookings. Pricing and marketing are developed around the asset and the buyers likely to evaluate it.
That preparation also addresses the transition: showings around guest stays, future reservations, furnishings, management agreements and the documents a buyer needs to review. Jack’s national short-term rental network broadens the conversation while the property-specific work gives it substance.
See the STR selling approachA SPECIALIZED PRACTICE. A WIDER CONVERSATION.
Jack’s work building an STR advisory practice and Compass’s short-term rental division has been covered in investment and business publications. Explore the coverage and the thinking behind the practice.
Read the STR press coverageFROM AN STR INVESTOR
“Jack’s knowledge of short-term rentals goes far beyond what we had experienced with other real estate agents. He understands the actual business behind the property.”
Frank M. · Short-term rental owner
Read Frank’s full reviewYOUR NEXT STR DECISION
Considering an acquisition or preparing to sell? Start with the address, your timeline and what you want the investment to accomplish. Jack will help identify the work that comes next.