But perhaps you would be better served helping a local experienced investor find deals and ask them to show you exactly how they analyze deals, what's good vs bad, how do they finance (debt vs equity) etc etc and understand their business model that has a proven track record by providing value to them.

Start small with duplexes or triplexes, analyze deals carefully, and build a team of local experts.

Listen to as many podcasts as you can and attend all of your local meetups to connect with other investors.

Is there anyone in your local market you could take out to lunch who does flips?

.✅ Hands-On Experience – If you plan to grow your real estate portfolio, managing tenants yourself can teach you valuable lessons about leases, maintenance, and local rental laws.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

Hello Sheree, A good place to learn about wholesaling will be going to the local REIA.

However, I am also considering duplex and tri-/quad-plex assets if they pencil.Additionally, I currently work for a locally-based commercial developer/lender on multifamily, land, and some hospitality projects.

Since you're in Destin, you might want to check with local firms that have experience with STR-heavy communities, as they’ll be familiar with the risks and requirements.

I found a 4 BR home next to local hospital. 

Also, happy to connect and share insights on market trends and local contractor recommendations.