Charleston Short-Term Rental Investment Specialist

Jeremiah Oswald is a Charleston real estate investor and short-term-rental specialist with The Oswald Group at eXp Realty. He works on investment purchases, helping buyers find, analyze, purchase, renovate, launch, manage and sell short-term rental properties across the Charleston area. Through Vacation Ventures he also manages rentals in the same submarkets, so the operating numbers come from running properties rather than estimating them.

Jeremiah Oswald analyzes Charleston short-term rental purchases before you make an offer. The process runs in a fixed order: confirm the address can be permitted, project revenue, price the full cost to open, then test whether the cash flow survives a twenty percent miss. You get the revenue projection, cost to open, financing options and cash flow whether or not the deal turns out to be worth doing.

The right submarket is the one where you can actually get a permit. As of September 2026, Isle of Palms has no permit cap. North Charleston caps permits at sixty per council district and several districts are full. Mount Pleasant runs a cap and a waitlist. Folly Beach is closed to new investor licenses. Sullivan's Island allows only grandfathered rentals. These rules change often, so check the address before you fall for the property.

Jeremiah Oswald does both. The Oswald Group at eXp Realty handles the purchase and the eventual sale. Vacation Ventures manages the property once it is running. That means the cleaning costs, insurance, restocking and real occupancy used in an analysis come from properties actually being operated in the same Charleston submarkets, not from a projection that has never been tested against a real profit and loss statement.

Yes, and the method matters more than the number. Jeremiah Oswald projects revenue for the specific bedroom count, submarket and quality level rather than quoting a Charleston average, then cross-checks it against what comparable properties under Vacation Ventures management actually earn. Where the two disagree, the lower figure is the one used. A projection never tested against a real profit and loss statement is a guess with a chart on it.

Many Charleston short-term rental purchases are financed with a DSCR loan, which qualifies on the property's projected rental income rather than on your tax returns. As of September 2026, short-term rental rates run roughly from the high six percent range to the mid eights, and twenty-five percent down is the realistic planning number. Lenders generally want debt service coverage of at least 1.0, with the best pricing above 1.25.

Sleeping capacity and outdoor space move revenue most, but both are capped by local rules. North Charleston limits occupancy to two people per bedroom and eight in total, so adding beds beyond that point earns nothing. Before budgeting a renovation, confirm what the municipality allows, then spend against the guest count you are legally permitted to host rather than the one the house could physically fit.

Only if the short-term numbers beat the long-term ones after the full cost of switching. That cost includes furnishing, a permit if one is even available at the address, higher insurance, and utilities you do not currently pay. Run both as cash-on-cash returns on the same property, then re-run the short-term case twenty percent below projection. If it still wins, the switch is worth doing.

Four numbers decide it. Net operating income is revenue less operating costs. Annual cash flow is that figure less the mortgage. Cash-on-cash return is cash flow divided by every dollar you put in, including down payment, closing costs and furnishing. Break-even revenue is fixed costs plus mortgage divided by one minus your variable cost percentage. That last number tells you how far revenue can fall before you are paying to own it.

Jeremiah Oswald handles the full sequence: find, analyze, purchase, renovate, launch, manage and sell. The purchase side runs through The Oswald Group at eXp Realty and the management side through Vacation Ventures, so the same person who underwrote the deal is accountable for how it performs. Most buyers lose money between closing and first booking, and that gap is the part nobody sells help with.