Mid-term rentals is also a strategy worth exploring, a good book to read on that is "30 day stay" by Zeona McIntyre & Sarah Weaver.  

best of luck on your journey. i would partner up with a reputable mentor if this is your first deal.

Of course, happy to connect you to local agents if you want to explore possibilities. 

As a fellow Chicagoan, I understand your reasoning for exploring opportunities outside of Illinois.

Spain is also another promising market we’ve been exploring, particularly for its growing tourism and rental opportunities.Currently, we’re also reaching out to US investors who might be interested in exploring these markets with us.

A broker who can also deliver a reputable management company (themselves or an independent company) willing to take over management at closing is a real plus for any residential rental investment. 

I’m particularly interested in collaborating with like-minded investors and exploring partnerships for larger acquisitions.Looking forward to learning from this community and connecting with others passionate about multifamily investing.Excited to learn and connect with you all!

If your HOA would allow it, I'd definitely explore that since you'd be back in town for a few months out of the year. 

Areas like Lawrenceville and East Liberty have undergone huge transformations.. it’s worth exploring how those shifts could affect your property’s future value.What’s your take?

Viator could also be a good option to explore.