We plan to hold on to them for a long time.  

I would consider selling if you have lived in the home the past 2 / 5 years since you have a decent amount of tax free equity in there but as long as you have a plan to reinvest those funds.By your numbers, since you have an amazing rate and high rents, I would consider renting it out if you believe your area will continue to grow in value.

I would also focus on landlord friendly states if you are planning to rent.

@Brett Jurgens,With strong equity and a good tenant, you have a few options:Cash-Out Refinance: Offers lower, fixed rates for stable monthly payments and lets you keep the property while using equity to invest in another rental.HELOC: Provides flexible access to cash, though with typically higher, variable rates that can fluctuate over time.1031 Exchange: If you're open to selling, a 1031 exchange could defer taxes and allow you to trade up to a higher-value property or diversify into a different market.Each option has pros, so it really depends on whether you want to hold onto the current property or leverage its value for something new.

How Ford’s BlueOval City Project Impacts Real Estate: A Setback and Opportunity for InvestorsFord’s massive BlueOval City project, a planned $5.6 billion electric vehicle (EV) manufacturing campus in Stanton, Tennessee, is a game-changer for the region.

Since you plan to travel often, focusing on systems and building a reliable team: agent, lender, property manager, and contractor. 

It’s easy to get caught up in the excitement of a potential deal, but skipping this step can lead to costly mistakes.Getting your real estate license is also a solid strategy just realize once you have a license wholesaling may not be in the cards as its a very gray area.Lastly, since you're planning to buy properties for yourself in 2026, start laying the groundwork now.

This has become challenging due to an increased interest in the historic district in Dubuque due to revitalization plans that include 18 million dollar investment into the historic downtown area. 

I plan to hold unless the rules change.  

I am still living in Chicago but plan to move to New York in a year or two.