Hey everyone,I’m comparing two 3-unit properties in Chicago and could use some insight from local investors.Option 1 – South Side (near Woodlawn area):Priced around $830KModern finishes, newer construction styleCurrent rents around $2,195, $2,000, and $2,000The area has a lot of new developments and new 3-flats going upMy concern: with so many new buildings being added, there’s likely going to be more rental competition, and property taxes may jump once reassessments catch up to all the new construction.Option 2 – Pilsen area:Priced around $735KAlso modern updates but smaller units (two 2-beds and one 3-bed)Taxes are currently low, but likely because the property hasn’t been reassessed since the recent renovationsThe area feels more established, with strong tenant demand and characterSo I’m weighing the growth potential and higher risk in the newer South Side market versus the more stable rents and potentially upcoming tax adjustments in Pilsen.Would you lean toward the newer-construction area with possible tax jumps but longer-term appreciation upside, or the lower-tax, established neighborhood that might get hit with reassessment later?

Eventually you'll start developing relationships with people in the market that will bring you off market deals, but they have to believe that you can close the deal.

The location requirement was not listed in the terms we captured at signup.She continued pushing the issue and eventually received the $500 through Venmo.I’m curious if other hosts had a similar experience.If you signed up under this promotion and were denied, you may want to:• Review your original signup emails or screenshots• Ask VRBO to review the original promotion terms• Escalate the case if necessaryIf multiple hosts experienced this, it may indicate a larger issue with how the promotion was handled.

and as you note marcus I use it like google.. what I have seen though I my wife uses it a ton.. and not all information is correct when it comes to land use and development..

My goal is to eventually purchase a multi-family home as an investment property.

I currently have access to several strong land opportunities suitable for development and am seeking investor(s) funding to move the projects forward.

My business parter has developed a database that scrapes all this data from county websites.

For those interested to know how developers turn raw land into approved residential lots, here are a few thoughts from someone who does this everyday.  

Investors who’ve actually run the numbers know better too.What makes this niche interesting isn’t just the demand (which is strong), or the margins (which can be excellent), but the control you have over the outcome if you build it the right way.In a phased development model, the biggest value drivers happen long before the first guest checks in:choosing land with the right zoning pathdesigning infrastructure that can scale without reworksequencing buildout so the project pays for its own growthmatching site mix to real demand, not assumptionsbuilding a guest experience that earns repeat stays, not just bookingsOnce those pieces are right, the downside shrinks fast.You’re not relying on one tenant type, one lease structure, or one rent assumption.

That’s why I dove into market data (vacancy trends, income growth, population shifts, and bedroom-level cash flow) and eventually built Heatmap Housing to make analyzing ZIP codes faster and smarter.I’d love to connect with other investors scaling out-of-state or looking to grow past the early stages.What markets are you keeping your eye on for 2026?