All Forum Posts by: Matthew Tregoning

Hey BiggerPockets Community!

I wanted to share our personal experience with a "Live-in" flip at the age of 21. My girlfriend and I embarked on this adventure, and I'm excited to walk you through our journey, from securing a 3% conventional financing to smart renovation choices.

1. The Financing: At 21, conventional financing might seem like a mountain to climb, but we discovered that it's entirely doable. We utilized a 3% conventional loan, which made our entry into the real estate market much more accessible. The lower down payment requirement allowed us to preserve our capital for renovations.

2. The Property: Our canvas was a 3-bedroom, 2-bathroom home that had seen minimal updates since the '80s. We saw potential in this fixer-upper nestled in a promising neighborhood. Location was key for us, as we believed in the long-term growth of the area.

3. The Strategy: Living in the property for a year while renovating was a game-changer. We strategically focused on high "bang-for-buck" renovations, such as transforming the outdated interiors. We decided to paint the old cabinets and replaced hardware, which saved us money while giving the kitchen a fresh look. We also opted for new countertops to modernize the space.

4. Sweat Equity: Our sweat equity was our biggest asset. We dedicated evenings and weekends to the renovations, learning valuable DIY skills along the way. It was hard work, but it significantly reduced our renovation costs.

5. Transitioning to Rental and Leveraging VA Loan:

After living in the property for a year, we made a strategic move. We transitioned it into a rental, providing a steady income stream while we used our VA loan to purchase a different property before moving out.

6. Selling for Profit: A year later, we decided to sell our live-in flip turned rental property. By this time, our smart renovations had boosted its value. We made a profit on the sale, which we reinvested in our next venture—a vacation rental property.

Our live-in flip at 21 was an incredible learning experience that allowed us to enter the real estate market while minimizing our financial risks. It's proof that age is just a number when it comes to achieving your real estate goals.

If you have any questions or want more details about our journey, feel free to ask. We're here to share and learn together!

Thanks,

Matthew

Quote from @Trent Reeve:

Quote from @Matthew Tregoning:

2. Seasonality Matters: Florida's vacation rental market is deeply influenced by seasonality. The winter months, when many visitors from colder states flock to Florida, tend to see peak demand and higher rental rates. On the flip side, summer offers a different kind of appeal, especially for families on school breaks. Understanding these seasonal trends is crucial for optimizing your rental income.

 cannot agree. there is an off-season in Florida. maybe certain areas, but especially along the panhandle, you see rock bottom rates or some people even close their property for the winter. i have not seen the "peak demand and high rental rates". most in my area have very empty calendars right now

I appreciate your perspective, and you're right that Florida, like any travel destination, does experience seasonal variations in demand and pricing. While certain areas, such as the theme park regions and coastal cities, may maintain relatively stable demand, other areas, including the Panhandle, can indeed have off-peak seasons where rental rates are lower, and some properties may close for the winter.

It's important to note that Florida's vast size and diverse regions can lead to different market dynamics in various locations. From my understanding, areas like Destin, for example, tend to experience a significant surge in demand during the summer months when visitors flock to enjoy the beautiful beaches and activities. This peak season can often make up for the slower winter months.

In my markets, I tend to see downtown in September and May. But we make up for this by discounting a few months in advance and tend to still maintain above 80% occupancy across all properties. Understanding the unique dynamics of your specific area is key to making informed decisions as a vacation rental property owner or guest. Different regions within Florida have their own seasonal patterns, and finding the right balance between high-demand and off-peak periods can be a strategic approach for vacation rental owners. Thank you for sharing your insights, and it's always valuable to consider the specific context of your property's location. 

Quote from @Michael Smythe:

How many doors you have now?

I have 9 doors now

Quote from @Ryan Thomson:

@Matthew Tregoning great job! House Hacking is certainly a game changer. I'm working on number 5 here in Colorado Springs. I tell my clients as much as I can of the awesome returns that house hacking provides. 

House hacking is the real deal, and it's awesome to witness your success with it in Colorado Springs. Sharing the magic of this strategy with clients is like revealing a hidden treasure chest of investment potential. Keep rockin' the house hacking game, and here's to many more prosperous ventures ahead!

Quote from @John Underwood:

A huge concern is getting insurance at all or if you're lucky a very elevated price due to the recent hurricanes.

Good Point! Elevated insurance costs due to the hurricane risk are a significant consideration in our initial financial analysis. Local agents are usually our "go-to", and seem to have a higher success rate for finding coverage. We've had multiple (5+) denials on some of our past short-term rental properties before finally getting an agent to cover us. 

Hey everyone,

I wanted to share a bit about my personal journey with house-hacking because it's a strategy that has truly changed my life. A few years back, I took the plunge and invested in a beachside duplex, and I haven't looked back since.

The Beachside Duplex: A Game-Changer

I discovered that finding a property where you can use one side as a vacation rental (think Airbnb) is one of the best strategies to fast-track your journey to financial independence. Here's why it's been a game-changer for me:

1. Double-Duty Property: With a duplex, you get the best of both worlds. You have a place to call home while also having the opportunity to generate income from the other unit. It's like having your cake and eating it too!

2. Location Matters: Being beachside was a huge win. It attracted vacationers looking for that sun, sand, and surf experience. Plus, the allure of the beach meant I could charge premium rates, especially during peak seasons.

3. Early Financial Independence: Thanks to the income from my vacation rental, I've been able to accelerate my path to financial independence. The rental income helps cover my living expenses, and it's a feeling of financial security like no other.

4. Managing on My Terms: Being in control of my Airbnb property management allows me to decide when I want to host guests and when I want some downtime. Having the flexibility of using the property as a short-term rental or mid-term rental for travel nurses or "snow-birds" in the winter has been a game changer.

5. Learning by Doing: House-hacking has been an incredible learning experience. I've gained firsthand knowledge about real estate investing, property management, and the vacation rental market. It's been a valuable education that money can't buy and has helped me in all deals after.

6. Pursuing My Passion: Perhaps the most remarkable part of this journey is that it allowed me to leave my job in the military and pursue my dream of being a full-time real estate investor. It's a path I had always wanted to take, and house-hacking provided the financial foundation and freedom to make it a reality.

Sharing the Dream

If you've been considering house-hacking or investing in a property that can double as a vacation rental, I can't recommend it enough. It's a strategy that's not just about building wealth; it's about creating a lifestyle that aligns with your goals and dreams.

Feel free to ask me any questions about my journey or if you're curious about how you can embark on your own house-hacking adventure. Remember, financial independence is within reach, and house-hacking might just be the key to unlock it.

I've been doing some deep diving into the short-term rental markets here in Florida, and I'm excited to share some insights with you. Florida has always been a hotspot for vacation rentals, and the market is as vibrant as ever. Here are a few key takeaways:

1. Diverse Opportunities: One thing that's striking about Florida is the diversity of short-term rental opportunities. From the theme park mecca of Orlando to the sun-soaked beaches of Miami and the Gulf Coast, there's something for everyone. Whether you're into urban getaways, coastal retreats, or serene lakeside escapes, Florida's got you covered.

2. Seasonality Matters: Florida's vacation rental market is deeply influenced by seasonality. The winter months, when many visitors from colder states flock to Florida, tend to see peak demand and higher rental rates. On the flip side, summer offers a different kind of appeal, especially for families on school breaks. Understanding these seasonal trends is crucial for optimizing your rental income.

3. Regulatory Landscape: Keep in mind that Florida's short-term rental regulations can vary significantly from one city or county to another. It's essential to stay up-to-date with local rules and regulations to ensure compliance and avoid any potential issues. This can include licensing requirements, occupancy limits, and tax considerations.

4. Theme It Up: Theming your rental property can set you apart in this competitive market. Florida's known for its theme parks and attractions, so why not bring a touch of that magic to your rental? Think Disney-themed decor in Orlando or a coastal-inspired vibe in beachfront properties.

5. Local Partnerships: Building strong relationships with local service providers, such as cleaning companies, property managers, and maintenance crews, is key to success. Florida's popularity means you'll have a steady flow of guests, and ensuring a seamless experience for them is essential for repeat business and positive reviews.

6. Technology and Marketing: Leveraging technology and online marketing is a must. Platforms like Airbnb and Vrbo are powerful tools, but also consider having your own website to showcase your property. Great photos, detailed descriptions, and engaging social media can help your property stand out in the crowded market.

7. Evolving Trends: Lastly, keep an eye on evolving travel trends. The pandemic has reshaped the way people travel, with more emphasis on remote work and extended stays. Consider catering to these trends by offering amenities like high-speed internet and comfortable workspaces.

Florida's short-term rental market is thriving, and with the right approach, it can be a rewarding investment. If you're considering jumping into this market or expanding your portfolio, make sure to do your research and stay adaptable to the changing landscape.

Thanks for sharing this insightful research and write-up on some fascinating vacation rental markets. It's clear you've done your homework, and I found it really interesting. Here are some thoughts on each market:

Wilmington, NC: It's great to see how Wilmington combines the charm of a coastal town with the added appeal of its historic sites and downtown area. The presence of a university, military, and a major production facility certainly adds to its rental potential. This diverse range of attractions is a real plus for investors.

Park City, UT: Park City's blend of outdoor activities, from skiing to hiking and biking, makes it a year-round destination. The Sundance Film Festival also adds a unique draw for visitors. It's interesting to see how a place known for winter sports can offer so much more.

Annapolis, MD: Annapolis seems like a hidden gem for vacation rentals, with its waterfront location offering a wealth of activities. The potential for revenue, despite a slightly lower occupancy rate, is encouraging, especially considering the water-based attractions.

Stowe, VT: Stowe's mix of outdoor activities, festivals, and events, coupled with its culinary scene, makes it a well-rounded destination. It's not just a winter wonderland; it offers something for visitors throughout the year.

Southampton, NY: Despite the seasonal nature of Southampton's market, the high-earning professionals from nearby NYC willing to pay top dollar during the summer months make it an attractive investment opportunity. The potential for substantial returns during peak season compensates for the lower occupancy rate.

Your insights on these markets are spot on, and I'm sure many investors will find this information valuable when considering their next vacation rental venture. Thanks again for sharing!

Sounds like you really nailed that investment deal! Your approach to timing, negotiation, and using your knowledge of the market paid off big time. I'm impressed by how you managed to secure the seller credit and navigate the appraisal gap.

It's also awesome to hear that you persevered through 30 offers to snag this opportunity. The competitive real estate market can be tough, but your determination definitely paid off.

Thanks for sharing your experience and insights. It's inspiring for those of us looking to make savvy investments. Keep up the great work, and here's to more successful deals in the future!

I'm adding EV Chargers in most of my STRs to stand out. Very few comparable properties in my markets have them, so I want to put myself in rare company.