Real Estate Consultant · Chicago, IL · Member since 2026 · 2 posts · 1 vote
I've been doing property due diligence for STR investors and here are the questions that sometimes get overlooked:
What jurisdiction actually governs the property?
What is the zoning classification, and does it allow the proposed use?
Are STRs permitted, restricted, capped, or prohibited?
Is a license or permit required, and is one currently obtainable?
Does an existing STR permit transfer with the property?
Are there deed restrictions, restrictive covenants, or HOA rules that create another layer of restrictions?
Are there septic, wastewater, parking, occupancy, or access requirements that could affect feasibility?
I’m curious how other investors approach this.
At what point in your acquisition process do you investigate these questions? Before underwriting, after identifying a promising deal, or only once you’re preparing an offer?
I'd want those questions answered before getting attached to the furnishing plan. I'd also have a local cleaner walk the actual house early. A place can look straightforward in photos and turn out to have a long driveway, awkward laundry setup or access problems that make every turnover harder. Those are useful things to learn before you're committed.
Since I work mostly the same areas (Hillsborough, Pinellas, Manatee, Sarasota counties FL) I know all of these already my memory. This is why its important to work with an STR knowledgeable agent in your given market to lean on their expertise. Always double check their work before closing the property but working with a good agent who specializes in STR can save you a lot of time and potentially money cutting the learning curve.