Ensure they’ve successfully completed similar projects on time and within budget.

Quote from @Duane Williams: We’re a family-owned fix-and-flip company operating in San Antonio, TX, and Northern Virginia, managing everything in-house—from wholesale acquisitions to rehab & construction (with our own project managers and crews) to listing & selling through our licensed brokerage.

Also, my worst performing project the past few years was a center city ground up project.

You run the numbers on the project and stress test it.

First year projection was 2-4%.

The city’s diverse workforce, combined with new developments and infrastructure projects, ensures that there is a consistent pool of renters, which can result in reliable cash flow for property owners.Finally, the Detroit real estate market is supported by numerous incentives for investors.

Make sure to prepare a professional proposal, highlight your STR track record, and be transparent with your financial projections.

If part of the property is rentable while renovations are happening, that could help offset carrying costs.Given your construction background, you’ve got a huge advantage in managing the project efficiently—it’s just about getting through the red tape and de-risking the unknowns before pulling the trigger.Have you talked to any local investors or contractors who’ve tackled similar projects in Wicker Park?

In a previous life I projected managed 54 new builds and have done my own flips to stabilize my own neighborhood.

I was on a ZBA meeting last week for one of our hotel projects.