The Oswald Group at eXp Realty

Charleston Short-Term Rental Investment Specialist

Jeremiah Oswald is a Charleston real estate investor and short-term-rental specialist. He helps investors find, analyze, purchase, renovate, launch, manage, and sell profitable short-term rental properties across the Charleston area, through The Oswald Group at eXp Realty.

Buying a short-term rental takes more than finding an attractive property. The purchase only works if the numbers work, and the numbers turn on things a listing never mentions: what the property can realistically earn, what it costs to furnish and run, how a lender will treat projected rental income, and what it will be worth to the next buyer.

Raised Charleston Lowcountry vacation rental home at golden hour with a double piazza and a tidal marsh behind it

From the first showing through to resale

  1. 01

    Find

    Identify properties that can perform as rentals, not just properties that show well.

  2. 02

    Analyze

    Model revenue, operating costs, financing and cash flow before an offer goes in.

  3. 03

    Purchase

    Negotiate and close with the rental use accounted for in the terms.

  4. 04

    Renovate

    Scope the work that actually changes what the property earns, and price it.

  5. 05

    Launch

    Furnish, photograph, list, and get it booking.

  6. 06

    Manage

    Run the day to day through Vacation Ventures.

  7. 07

    Sell

    Reposition or exit, priced on what the property produces and not on comparable sales alone.

What we look at before you buy

Every property is evaluated from acquisition through operation, not just through to closing.

Projected revenue
What comparable rentals in that specific submarket actually earn, by season.
Financing
How the loan is structured, and how a lender treats projected rental income.
Renovation cost
The work required to make it rentable, and the work that raises the nightly rate.
Furnishing
The full setup cost, which is rarely in anybody's first budget.
Guest capacity
How many the property sleeps, which is the single biggest lever on revenue.
Management expenses
Cleaning, turnovers, platform fees, maintenance, and the management fee itself.
Cash flow
What is left after the mortgage and every operating cost.
Resale potential
What it is worth on exit, to an investor rather than to a family.

Where we work

Across the Charleston area and the Lowcountry.

  • North Charleston
  • Hanahan
  • Summerville
  • Mount Pleasant
  • Goose Creek
  • Ladson
  • Moncks Corner
  • The beach towns
Aerial view of Lowcountry tidal creeks and waterfront homes across the Charleston short-term rental market

These submarkets do not behave alike. Guest demand, nightly rates, seasonality and local short-term rental rules all differ from one to the next, and a property that works in one can fail in another a few miles away.

Living room of a furnished Charleston short-term rental with navy sofa, rattan chairs and marsh views through plantation shutters

Vacation Ventures

The property still has to be run

Once a rental is bought and launched, somebody has to operate it. That is Vacation Ventures, a short-term vacation rental management company under The Oswald Group.

It matters here for one reason. The revenue and expense figures in an analysis come from running rentals in this market, not from a spreadsheet estimate. Most agents selling investment property have never had to make one work after closing.

Start with the numbers

If you are weighing a specific property, or working out whether a Charleston short-term rental makes sense at all, the first conversation is about what it would actually earn and what it would actually cost to run.

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