@Kevin Zmick the rental market in Chicago can be very, very seasonal.

I have a lengthy Legal Opinion, from my seasoned Legal Team regarding this matter.

We are about 40% full for the season right now and we are waaaay out of town.

These costs begin to add up over time.I know for some seasoned investors, and for the sharks out there this probably sounds ridiculous.

If you get enough experience doing exactly what you did with your first property there are lenders that would no require your purchase to "season".

I would at least start there and good timing to figure out a plan with spring slowly approaching and our busier sales season in WI.  

The resources are endless here, but at some point, the messier it gets, the less seasoned investors are going to spend the time.

@Gash Nookala,Renting can indeed be slower in winter, but here are some tips to boost interest:Enhance Listing: Ensure your listing has detailed descriptions and high-quality photos—consider professional photography if needed.Competitive Pricing: Double-check local comps; even a slight price adjustment or incentives (like a reduced deposit) could attract more interest.Broaden Marketing: Beyond Zillow, Hemlane, and MLS, use social media, community boards, and local business connections to reach a wider audience.Flexible Lease Terms: Offering shorter or month-to-month leases might appeal to tenants during this slower season.Local Property Manager: A local pro can tap into their network and help fill the vacancy faster.These steps should help you find a tenant despite the seasonal slowdown.

Johnson City could be a great spot for STRs, especially if you focus on hospital staff rotations, visiting professors, or traveling professionals, which would balance out any seasonal dips in tourism.For STRs, consider targeting weekend travelers exploring the Appalachian Trail, Boone Lake, or local festivals.

It was really insightful, especially the part about how DSCR loans offer shorter seasoning periods and more flexible qualification requirements compared to conventional financing.I’m currently focused on scaling into 6+ unit multifamily properties in New Jersey using the BRRR strategy.