1st-Time Buyer in Oahu, Using VA Loan, Family of 4, Looking to Start Investing Smart

[Brant Lamberth]

Hi everyone,

I’m stationed in Oahu and planning to use my VA loan to purchase our first home between December 2025 and February 2026. I’m a first-time homebuyer with a wife and two young kids, and we’re treating this as the beginning of our real estate investing journey.

We’re exploring options like:

• A duplex/triplex/fourplex for house hacking
• A single-family home with an ADU or rentable space
• Possibly finding an assumable VA loan if the numbers work

Our long-term goal is to build a real estate portfolio, but we want to start the right way—with a property that makes sense now and can serve as a solid rental later.

Since this will be our first home purchase ever, I’m also looking for advice from those who’ve been down this road:

• What should I be thinking about or doing right now to prepare?
• What mistakes should I avoid as a first-time buyer and future investor?
• How can I evaluate a home for both personal living and future rental value?

I’d also love to connect with like-minded investors here in Oahu, especially military folks or anyone who started small and built up. If you’re open to sharing your experience or mentoring someone who’s eager to learn and take action, I’d be incredibly grateful.

Thanks in advance for any insight, tips, or connections!

– Brant