Because you realistically won’t be covering the expenses of the property where it justifies the risk or investment.  

This protects against potential claims and liabilities specific to the rental.For tax purposes, maintain clear records of rental-related income and expenses, allowing deductions for insurance, utilities, maintenance, and depreciation proportionate to the rental unit.

Quote from @Jay Hinrichs: Oregon finally passed legislation to reel in unlicensed wholesaling its in this months publication from the state RE agency.Highlights:Goes into effect  July 1 2025Requires:On line application to become a licensed wholesaler  ( RE agents exempt from this of course they already have licenses)Name of company and individuals who will be performing these services.Each one needs a full criminal background check and approval prior to receiving the license.300.00 annual fee for the license.Written Disclosures in Bold 10 point.These must be given to Buyer and Sellers prior to entering into a wholesale contract and signed for.Also RE brokers assisting wholesalers need to give these to potential buyers and sellers.

Now I'm really torn, but think it just has to kill it for the issues of risk.

Each potential buyer has come to their own conclusion that it would be too much hassle and risk to manage in this fashion vs a traditional rental even though the average cap rate in our area has been half that at best.

Cost per lead (CPL) is crucial—it shows how much you're paying to get a potential seller or buyer’s info, and you want this as low as possible without sacrificing quality.

Maybe there is severe hurricane risk, but it is something I would look into. 

Hi, you seem like a potentially good candidate for DSCR Loans, a loan product that was essentially designed for exactly this - investors that want to build a portfolio relatively quickly and not be slowed down by DTI requirements or other hassles from conventional options.Would be glad to help, also check out this 12-part series published here on BP on everything you would ever want to know on this loan option!

Obviously some potential issues with the lender, but how often do these deals really happen?  

Additionally, there’s always a risk that any pet-related damages could be hidden under furniture or otherwise concealed, potentially leaving us to cover the costs if the security deposit is fully depleted by other expenses (e.g., damages or unpaid rent).