I'm in my early 30s, married, with one child and another on the way. We're planning to move three hours away soon.

Currently, we own one Class A rental property that generates about $500/month in cash flow. Additionally, we have a decent amount invested in retirement accounts, which we plan to continue building over time.

As part of the move, we’ll be purchasing a larger home. While I love the idea of eventually owning a paid-off primary residence, I’m debating whether it’s smarter to sell our current house and use the equity as a down payment on the new home or to keep it as a rental. I wonder if the disciplined, long-term play is better than having the cash now. However, I’m unsure about the utility of having two paid-off rentals 25 years from now. Is selling now a mistake? I’d appreciate your perspectives.

Here are the details about our current home:

• 3/2 Class A property in a middle-America town with historically ~1% annual appreciation.
• Purchased in 2020 for $200,000 at a 3% 30-year fixed rate.
• Remaining mortgage: $150,000.
• Estimated value: $270,000 (based on recent sales).
• After selling costs: Likely $100,000 in net proceeds.
• Rental potential: $2,000–$2,300/month.
• PITI: $1,200/month ($700 mortgage + ~$500 insurance/taxes).
• Maintenance/CapEx/Vacancy (20%): ~$400/month.

If kept as a rental:

• Net cash flow (self-managed): ~$500/month or ~$300/month with property management.
• Low appreciation potential but ~$400/month in principal paydown.

Considerations:

1. What’s the additional overhead of managing a second rental property remotely (3 hours away)?
2. The house has a new roof, but HVAC and water heater replacement might be needed in the next few years.

Also, mortgage rates are currently around 7%. Selling would allow me to put the $100,000 equity toward the new primary home, potentially avoiding a larger loan.

What would you do in this situation? Is it smarter to hold onto the house and keep renting it out, or sell now and roll the equity into the new home?