Most Common Questions Asked in Real Estate Investing

Real insight from those doing it every day—straight from the Marsh Lending Roundtable.

Thinking about jumping into vacation rental or investment property ownership? You’re not alone. But before you start dreaming of summer bookings and beachside returns, you probably have a few big questions—about financing, property strategy, and whether it’s even the right time to buy.

What’s the biggest mistake new investors make?

One of the first pitfalls? Looking at properties before you understand your lending options. Many new buyers treat an investment loan like a traditional mortgage, and that can quickly create problems.

The truth is: investment properties call for a different approach—different lenders, different products, and different expectations. Starting with a lender who understands investment lending (and ideally offers a range of products, not just one or two) can give you a clearer path forward before you ever step foot inside a home.

Should I get pre-approved first?

Absolutely. An educated buyer is the best kind. Pre-approval helps define your purchase power early, saving you time, narrowing your focus, and setting expectations before the property search even begins.

Understanding your appetite versus your capability is key. What can you afford now—and what will you actually be approved for under an investment loan scenario? Getting those answers upfront helps shape the rest of your strategy.

Is now a good time to buy?

In short: yes. Especially along 30A, where more inventory means buyers finally have options—and leverage. With fewer bidding wars and more opportunities to negotiate, smart investors can secure strong deals.

That said, if you’re looking to sell, timing depends more on your unique goals. For many, now may be the perfect moment to trade up. With equity gains from recent years, several investors are making moves from starter rentals into higher-performing properties that align better with their long-term income strategies.

How do I price my short-term rental?

This depends entirely on your goals. Some investors prioritize occupancy—booking as many nights as possible to maximize overall revenue. Others aim for a higher Average Daily Rate (ADR), accepting fewer bookings but at premium pricing to reduce wear and tear and maintain a luxury experience.

In most cases, the best strategy falls somewhere in the middle: enough weeks booked (around 30–34 per year) with a strong enough rate to generate sustainable income. Your management company can help craft a pricing plan based on the kind of property you own—and how you plan to use it.

What’s the best way to find off-market deals?

If you want to find great deals, you need a great realtor. It’s that simple. Many of the best opportunities never hit public listings. Agents with strong networks often know about potential sales before the general market does—and they reach out to trusted clients first.

Building a strong relationship with a local agent can give you early access to these opportunities, especially in a market like 30A where inventory moves quickly, and investor interest is high.
What should I expect during a home inspection?

In a word: surprises. But with the right inspector and experienced agent, you’ll be prepared to handle whatever comes up. A thorough inspection covers the home’s structural condition, major systems, and insurance-sensitive features like roof age. From there, your agent can help you negotiate repairs, credits, or post-closing fixes depending on your offer terms.

How do I market my property once I own it?

Visibility is everything. The right management company won’t just list your property—they’ll promote it through premium channels like Marriott Homes & Villas, Airbnb Luxe, and their own guest database. That kind of reach can dramatically improve your rental’s performance.

Many first-time investors try to self-manage but struggle to stand out in a sea of listings. Partnering with a pro gives your property the best shot at high returns, consistent bookings, and satisfied guests.

The path to passive income through real estate starts with asking the right questions—and getting answers from people who live it every day. Whether you’re figuring out financing, pricing your rental, or deciding who to partner with, the most important step is to build a team that knows what they’re doing and puts your goals first.

At Marsh Lending, we’re here to be part of that team. Learn more about how to make passive income with vacation homes and rentals on the Marsh Lending YouTube Channel.

Want help planning your next investment move? Contact Marsh Lending and let’s talk about your strategy.