Out of town investing can make sense precisely because it forces you to build proper systems and third party management from day one, instead of trying to do everything yourself.Indianapolis is a market many Chicago based investors look at for the reasons you mentioned: lower entry prices, more predictable cash flow, and fewer regulatory headaches than the city of Chicago.

That would be how predictable, obvious and simple the massive profit to come was. 

The predictable cycle is spot on. 

Catskills (NY): Strong demand + higher ADRs, but regulations are town-by-town and tighteningSome towns require STR permits, owner-occupancy, caps, or outright bansBuild costs, permitting, septic/well, and taxes are generally higherMore upside, but more friction and regulatory risk  Shenandoah Valley (VA): Generally more STR-friendly, especially outside town limitsZoning and permitting tend to be simpler and fasterLower land + build costs in many areasSlightly lower ADRs, but often more stable and predictable  If your goal is simplicity and fewer regulatory surprises, Shenandoah often wins.If your goal is top-line revenue and long-term appreciation, Catskills can work—but you have to be very precise about the town, zoning, and STR rules before buying land. 

From what I’ve seen working with experienced investors, the choice between private money vs. hard money usually comes down to a few very specific, commonly used criteria.Experienced investors usually weigh a mix of speed, certainty, and structure, and the right choice often depends on the deal’s timeline and complexity.Hard Money tends to win when:Speed to close is criticalThe borrower needs higher leverage or a more structured rehab draw processThe deal requires a lender who is used to assessing value and risk quicklyThere’s a need for predictable underwriting and a clear, repeatable processPrivate Money is often preferred when:Flexibility matters more than structureBorrowers want lower fees or a more relationship-based arrangementThe deal doesn’t require renovations or complicated funding mechanicsThe investor has long-standing trust with the lenderMost seasoned investors tell us they choose based on certainty of execution—who can reliably close fast, fund clean, and stay consistent from one deal to the next.

It is the predictable outcome of a use you likely selected because you wanted higher returns than renting the home to a single household.

Yet these threads predictably devolve into the same pattern.

However, in Madison, WI, I will see prices paid that won't cash flow after paying some assumed mortgage payment to acquire the property and even using the listing agent's predictions for higher market rents, so understand you wondering what am I missing or what are these buyers thinking, knowing sellers want the best terms they can get. 

2025 housing market gut check: Which predictions came true, and what can we expect in 2026?

Think in terms of “bankability,” not beauty.The best value adds:Reduce lender riskIncrease predictable incomeImprove functional utilityNot necessarily what looks best on Instagram.