To get started, continue learning through podcasts like the BiggerPockets Real Estate Podcast and books like "The Book on Rental Property Investing" and "Set for Life."

@Jared Goldwasseri would strongly recommend you go to Cincinnati in person. 

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

There is a lot you need to learn in order to make this strategy work and a lot of ways you can potentially stumble.

Well, STR can work well for people who own a vacation house for personal use, and just want to generate some extra income when not in use.  

Due to the current interest rates, you probably can't live for free, but you can definitely learn how to house hack in that first year, reduced your personal housing costs, learn the rent by room/co-living strategy on-site, and then probably break-even after move out, but most importantly, it is possible to make that work in 2025 with today's rates.It just takes being open-minded and willing to be flexible for the 1st year.  

@Richard Rafferty, given the relatively small nature you are looking to take on with your first syndication, personally, I would find it hard justify the typically 20-30k+ for a paid mentor. 

Better to invest in your backyard so you can learn and use your commissions for price reductions. 

.✅ 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.

We purchased it off market, as-is, and as it was our personal home, we renovated over time.