A few ridiculous photos below - I guess the current owners tried to make the most of the space and turned it into a literal "man cave" :)

Even if an inspection comes back with a foundation in disrepair or the roof is about to cave in or there's black mold behind every wall, the seller is still keeping the buyer's DD if the buyer cancels the contract.

Purchase price: $200,000 Cash invested: $200,000 Short Term Rental condo located on the Cave B Winery, overlooking the Columbia River Gorge, and within walking distance of the World-renowned Gorge Amphitheatre.

You're in somewhat of a sticky situation now as you do not want her to expect you to cave every time she asks for something, so you need to somehow strike a balance. $500 is steep, but I'd be inclined to offer maybe $250 off next month's rent and tell her that the expectation is that when she moves out the place will be spotless.

A multi STR on the water sounds delightful! 

@Michael Plante I caved and bought the parcel register.

Hello Zach, I would be delighted to have a visit with you. 

F/F lenders specialize in this type of property but wont lend if the roof is caved in or a wall is missing but its just renovations/upgrades, you wont have an issue with these types of loans.

Then with a backhoe, the sides can be caved in.

This is my first post, and I am delighted to have someone respond!