Building on My Rental Experience - Looking Forward to Grow & Connect!

Building on My Rental Experience - Looking Forward to Grow & Connect!

York, SC · Member since 2026 · 9 posts · 1 vote

Hi! I’m Jill, and I live in York, South Carolina, just outside of Charlotte, NC and Rock Hill, SC. I’m a single mom to a 10-year-old son and have a education in finance, along with over 20 years of experience in the insurance industry. I currently work in a field sales and underwriting role specializing in management liability insurance.

I’ve always been interested in real estate investing, and I’m finally getting serious about educating myself and taking the next steps toward building a rental property portfolio.

I currently rent out the lower level of my home as a furnished mid-term rental and am exploring the possibility of offering short-term rentals between longer bookings. I also own a travel trailer that I rent through RVshare, so I’ve gotten some hands-on experience managing rentals, working with guests, and learning the ins and outs of generating rental income.

My next big goal is to purchase my first standalone investment property and eventually build a portfolio that provides additional income, long-term financial freedom, and more flexibility with my time. I’m taking a practical approach, focusing on learning, saving, and making smart financial decisions along the way.

One thing I’m trying to figure out is what direction to take with my first investment property. I love traveling, especially to the beach, and I’m intrigued by the idea of purchasing vacation rentals in destinations my son and I enjoy visiting. I love the thought of generating income through Airbnb or VRBO while also having a place we can enjoy ourselves.

On the other hand, I wonder if it would be smarter to purchase my first investment property closer to home, where I can be more hands-on and gain experience before investing farther away. I’d love to hear from experienced investors about which direction they’d recommend and why.

I’m also curious how others balance real estate investing with a full-time career and family responsibilities, especially fellow single parents! Between working full-time, raising my son, and managing the rentals I already have, I’m interested in learning how others find the time to research properties, network, and grow their investments without spreading themselves too thin.

I’ve recently started listening to BiggerPockets podcasts and audiobooks, and I’m excited to learn from people who have already been down this road.

I’d also love to connect with other investors in the Charlotte, Rock Hill, and York County areas! I’m hoping to build relationships with like-minded people, learn more about the local market, and expand my network as I work toward my goals.

Looking forward to learning from this community, sharing experiences, and hopefully making some great connections along the way!

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Specialist · I give advice - [email protected] - I focus on states where investing is profitable, reasonably safe & secure · Member since 2026 · 125 posts · 39 votes
3d
Quote from @Jill Rhodes:

Hi! I’m Jill, and I live in York, South Carolina, just outside of Charlotte, NC and Rock Hill, SC. I’m a single mom to a 10-year-old son and have a education in finance, along with over 20 years of experience in the insurance industry. I currently work in a field sales and underwriting role specializing in management liability insurance.

I’ve always been interested in real estate investing, and I’m finally getting serious about educating myself and taking the next steps toward building a rental property portfolio.

I currently rent out the lower level of my home as a furnished mid-term rental and am exploring the possibility of offering short-term rentals between longer bookings. I also own a travel trailer that I rent through RVshare, so I’ve gotten some hands-on experience managing rentals, working with guests, and learning the ins and outs of generating rental income.

My next big goal is to purchase my first standalone investment property and eventually build a portfolio that provides additional income, long-term financial freedom, and more flexibility with my time. I’m taking a practical approach, focusing on learning, saving, and making smart financial decisions along the way.

One thing I’m trying to figure out is what direction to take with my first investment property. I love traveling, especially to the beach, and I’m intrigued by the idea of purchasing vacation rentals in destinations my son and I enjoy visiting. I love the thought of generating income through Airbnb or VRBO while also having a place we can enjoy ourselves.

On the other hand, I wonder if it would be smarter to purchase my first investment property closer to home, where I can be more hands-on and gain experience before investing farther away. I’d love to hear from experienced investors about which direction they’d recommend and why.

I’m also curious how others balance real estate investing with a full-time career and family responsibilities, especially fellow single parents! Between working full-time, raising my son, and managing the rentals I already have, I’m interested in learning how others find the time to research properties, network, and grow their investments without spreading themselves too thin.

I’ve recently started listening to BiggerPockets podcasts and audiobooks, and I’m excited to learn from people who have already been down this road.

I’d also love to connect with other investors in the Charlotte, Rock Hill, and York County areas! I’m hoping to build relationships with like-minded people, learn more about the local market, and expand my network as I work toward my goals.

Looking forward to learning from this community, sharing experiences, and hopefully making some great connections along the way!

With our new investors we alway sencourage a closer to home approach until they've worked through a couple of properties.

Since you have a background in finance you might look into using creative finance to buy the properties. That way you can take over someone's 4%+ loan and profit on the margin.

See this reply in the discussion

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  • Specialist · I give advice - [email protected] - I focus on states where investing is profitable, reasonably safe & secure · Member since 2026 · 125 posts · 39 votes
    3d
    Quote from @Jill Rhodes:

    Hi! I’m Jill, and I live in York, South Carolina, just outside of Charlotte, NC and Rock Hill, SC. I’m a single mom to a 10-year-old son and have a education in finance, along with over 20 years of experience in the insurance industry. I currently work in a field sales and underwriting role specializing in management liability insurance.

    I’ve always been interested in real estate investing, and I’m finally getting serious about educating myself and taking the next steps toward building a rental property portfolio.

    I currently rent out the lower level of my home as a furnished mid-term rental and am exploring the possibility of offering short-term rentals between longer bookings. I also own a travel trailer that I rent through RVshare, so I’ve gotten some hands-on experience managing rentals, working with guests, and learning the ins and outs of generating rental income.

    My next big goal is to purchase my first standalone investment property and eventually build a portfolio that provides additional income, long-term financial freedom, and more flexibility with my time. I’m taking a practical approach, focusing on learning, saving, and making smart financial decisions along the way.

    One thing I’m trying to figure out is what direction to take with my first investment property. I love traveling, especially to the beach, and I’m intrigued by the idea of purchasing vacation rentals in destinations my son and I enjoy visiting. I love the thought of generating income through Airbnb or VRBO while also having a place we can enjoy ourselves.

    On the other hand, I wonder if it would be smarter to purchase my first investment property closer to home, where I can be more hands-on and gain experience before investing farther away. I’d love to hear from experienced investors about which direction they’d recommend and why.

    I’m also curious how others balance real estate investing with a full-time career and family responsibilities, especially fellow single parents! Between working full-time, raising my son, and managing the rentals I already have, I’m interested in learning how others find the time to research properties, network, and grow their investments without spreading themselves too thin.

    I’ve recently started listening to BiggerPockets podcasts and audiobooks, and I’m excited to learn from people who have already been down this road.

    I’d also love to connect with other investors in the Charlotte, Rock Hill, and York County areas! I’m hoping to build relationships with like-minded people, learn more about the local market, and expand my network as I work toward my goals.

    Looking forward to learning from this community, sharing experiences, and hopefully making some great connections along the way!

    With our new investors we alway sencourage a closer to home approach until they've worked through a couple of properties.

    Since you have a background in finance you might look into using creative finance to buy the properties. That way you can take over someone's 4%+ loan and profit on the margin.

    • York, SC · Member since 2026 · 9 posts · 1 vote
      3d

      Thanks, John! I appreciate the advice. I've been leaning toward starting closer to home, especially since I'm still learning and juggling a lot. Your advice makes sense! I'm definitely interested in learning more about creative financing! Grateful for this forum.

  • Property Manager · Melbourne, FL · Member since 2019 · 353 posts · 150 votes
    2d

    Welcome, Jill! Your furnished rental and RV already give you a useful way to test how much hands-on work fits into your week. Before adding short stays between MTR bookings, I’d map out who handles the extra turnovers when you’re at work. Even a few gap bookings can change the rhythm quite a bit. Which part of your current rental setup takes the most time: guest messages, cleaning coordination, or maintenance?

    • York, SC · Member since 2026 · 9 posts · 1 vote
      2d

      Thanks Matthew! That's a really good point, and something I've been thinking about as I explore expanding into short-term rentals. So far, the furnished rental has been pretty manageable since my tenants typically stay 30-90 days. The RV requires a little more coordination, especially with turnovers and maintenance, but neither has been too overwhelming.

      I also work from home most days, and my furnished rental is in the lower level of my house, which makes managing it a little easier. I'm considering short-term rentals mainly as a way to fill gaps between midterm tenants rather than having it operate as a full-time Airbnb.

      I'm curious, as someone with experience in property management, at what point do you think it makes sense to outsource cleaning/property management versus handling things yourself?

  • Brad SeidBusiness Member
    Lender · Licensed in 28 States · Member since 2026 · 176 posts · 53 votes
    2d

    @Jill Rhodes Hi Jill! It’s great that you’re already building experience with rentals! If you’re considering purchasing your first investment property, I’d be happy to help you explore financing options that align with your goals. Feel free to reach out anytime. Wishing you success as you grow your portfolio!

  • York, SC · Member since 2026 · 9 posts · 1 vote
    2d

    Thanks Brad! When I’m at the point where I’m financially ready, I will certainly reach out.

  • Matthew MorrowBusiness Member
    Investor · PA - NY - NJ · Member since 2019 · 600 posts · 203 votes
    1d

    @Jill Rhodes Welcome! You're already ahead of most people starting out, running your own mid-term rental. Whichever way you go, being able to get eyes on the property and having a team you trust there makes a huge difference, especially with a full-time job and kids. The best part is real estate lets you control the game, building a better quality of life and a legacy for your family, something a job will never do. BP is a huge resource, so dive in. Best of luck!

    CORE Team | Realty ONE Group Supreme547 Reviews
    • York, SC · Member since 2026 · 9 posts · 1 vote
      1d

      Thanks, Matthew! I really appreciate the encouragement! Managing my mid-term rental has been a great learning experience, and I’m excited to continue learning and eventually expand into more properties. I completely agree that having a trustworthy team will be key, especially while balancing a full-time career and being a single mom. I’m excited to be part of the BP community and really appreciate everyone’s insight and willingness to share their experiences!

  • Financial Advisor · FL · Member since 2024 · 462 posts · 107 votes
    1d

    Welcome to the community, Jill! Balancing a finance career, parenting, and managing MTR/RV units is already impressive, you've got a great foundation.

    As a lender, we often see investors face that exact dilemma: local long-term vs. out-of-market vacation rental. Starting closer to home for your first standalone property usually makes balancing family and leverage much easier to manage. Once you have that first asset running smoothly, expanding into vacation markets using DSCR loans (where debt is qualified on the property's airbed revenue rather than your personal DTI) becomes a seamless second step.

    Wishing you huge success as you grow your portfolio!

    • York, SC · Member since 2026 · 9 posts · 1 vote
      22h

      Thank you, Stevan! I really appreciate the encouragement and insight. Starting locally and building from there makes a lot of sense, especially while balancing work and parenting. I’m excited to keep learning and eventually grow my portfolio!

  • Divin KanyamaBusiness Member
    Accountant · Seattle, WA · Member since 2025 · 470 posts · 190 votes
    17h

    Welcome, @Jill Rhodes ! You already have a great foundation—finance and insurance experience, plus hands-on practice with both a furnished rental and RVshare. That combination should help you evaluate risk and understand the operational side better than many first-time investors.

    For a first standalone property, staying reasonably close to home may be the simpler way to learn without adding travel and remote-management risk. A beach rental can be appealing, but personal enjoyment should be treated as a bonus; the deal still needs to work after seasonality, management, cleaning, insurance, maintenance, local regulations, and periods of personal use. Given your career and family responsibilities, a conservative local rental with reliable management and clear systems may offer the best balance. Connecting with Charlotte-area investor groups, property managers, lenders, and agents should also help you compare real opportunities before choosing a strategy. You do not need to scale quickly—one well-run property is a strong first step.

    • York, SC · Member since 2026 · 9 posts · 1 vote
      15h

      Thank you, Divin! I really appreciate your thoughtful advice. The more I learn, the more I’m leaning toward starting with a local long-term rental focused on consistent cash flow and saving the beach property dream for later. I’m taking this time to educate myself, build savings, and connect with other investors. I agree that starting with one well-managed property is a great goal!

  • Matthew MorrowBusiness Member
    Investor · PA - NY - NJ · Member since 2019 · 600 posts · 203 votes
    16h

    @Jill Rhodes you're welcome. Balancing that with a full-time career and being a mom is no small thing, so building the team early is the right call. Keep us posted as you grow.

    CORE Team | Realty ONE Group Supreme547 Reviews
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