New Investor | Tourism & Hospitality Pro Turning to Real Estate | Midwest Buy & Hold

[Chris Gasper]

Hi everyone! After being a silent member for over a year, I’m finally stepping into the light.

My name is Chris. I live and work in Key West, FL, where I’ve spent nearly 20 years in the tourism and hospitality industry. After two decades of working with people from all walks of life, the most important lesson I’ve learned is this: people will always remember how you make them feel. Whether you’re negotiating a deal or navigating tough conversations, emotional intelligence matters. Real estate is often a deeply emotional business — and how we treat others can leave a longer-lasting impact than any spreadsheet ever could.

Over the past year, I’ve been building a long-term strategy to transition into real estate investing as a core component of my financial future.

I’m focused on buy-and-hold SFRs and small multifamily properties in strong Midwest markets. My target metros right now are Pittsburgh, Kansas City, and Indianapolis. While I live in Florida, I’m aware of the risks and challenges that come with investing out of state — especially without boots on the ground. That’s why I place such high value on building trustworthy relationships with local professionals. I believe this community is one of the best places to start doing that.

I’m especially interested in networking to find off-market deals, and I’m in the process of developing repeatable systems for deal analysis and acquisition. I’m here to learn from those who’ve done it, contribute when I can, and eventually scale with a strong foundation and the right team.

If you’re active in these markets — or simply want to trade ideas — I’d love to connect. My goals here are to learn as much as possible, gain financial independence for my family, and give back to this great community.

Looking forward to getting more involved with the BiggerPockets family.

– Chris G.

[Terrance Hill]

Welcome, Chris! Love your approach—emotional intelligence is huge in real estate, and your focus on building relationships and systems will pay off big, especially investing out-of-state. For your target markets (Pittsburgh, KC, Indy), start by connecting with investor-friendly agents, property managers, and contractors—having a trusted local team is critical. Also, running your first few deals through BP calculators and analyzing numbers conservatively will give you confidence and help you avoid common mistakes.

Excited to see your journey and insights as you scale your portfolio!