One of our borrowers who successfully flips on the South Side (Dobson, Park Forest, etc.) is capitalizing on the abundance of discounted rehab properties (on market and off market via wholesalers and the such), which is a key strategy given rising rates. 

The markets investors like you want to live in and invest in are often two totally different places, so don't limit yourself yo a single plan. 

It’s a market where cash flow is achievable without needing a massive upfront investment.

No, you cannot create phantom losses this way.Some additional issues that we have not addressed:- holding rentals inside an S-corp has many tax disadvantages- you will likely jeopardize your $250k/$500k capital gain exclusion for homesteads- you will lose asset protection afforded to personal residences by most states- you will lose your homestead exemption for local property tax - your insurance will have to change from owner-occupied to rental, i.e. go up- and there's moreConclusion: there're reasons why nobody is doing this clever "strategy" but A+ for trying.

Have you all invested in other markets already or is this the first? 

Quote from @Michael Ewers: Hey y'all, Wondering what is the best marketing strategy for obtaining off market leads?

One I know is based in LA as that's a huge market of course..

One thing I’ve learned in land acquisition is that the approach has to change depending on the market.

How CIPS Has Helped Me So FarAccess to a Global Network: Through my CIPS connections, I can collaborate with real estate professionals in key markets such as Dubai, Portugal, and the Caribbean, where I see strong investment potential.Understanding Foreign Markets: CIPS training provides insights into market trends, regulations, and transaction structures that differ from domestic deals.Opportunities for Investors & Buyers: Many international buyers are interested in New York and Long Island properties, while U.S. investors are exploring opportunities abroad. 

The additions are usually small.Buy focusing on real high value places, you are putting yourself in a narrower guest pool.