We have offered to allow her to pay a reduced rent for the first few months as well but I am worried that may create some sort of limit on how much we can raise the rent on her in the future.

This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

:@Joshua SmithWay to go in reducing the principal balance of your primary residence.

There are some public sources (www.city-data.com) that can provide good baseline information.

I also invest in other assets such as stocks, and private companies as well. for RE agents I see absolutely no conflict.. its their job.. not every agent starting out can afford to buy a rental.. and note very agent even wants to own a rental ( like me) I only like to deal in land when I sold RE to the public .

Would encouraging longer stays realistically help reduce this, especially for a medium-sized cabin?

So if the deal goes right, I get a return in the form of equity on the house, and my rent is also reduced since let's say, as part owner, I would be receiving a portion of the rent (which I would be paying...).

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.

States that are non-disclosure don't have as much public information and Zillow doesn't have access to non-public info for their analytics. 

We have had to reduce nightly rates 30% just to get bookings in my area which is Port Saint Lucie, Fl.