For your first guests, go the extra mile—leave a welcome note, provide thoughtful amenities, and ensure the place is spotless.After their stay, send a friendly message like, “Thanks for staying!

I know it seems like a tough task, but can you spend a few more months or a year while you continue to learn to really tighten the budget or find ways to earn a little extra to start from a stronger position?

Vs her current super-chill life, get's special discounts all over the place for being "too poor" and all the while can work cash jobs when wants extra, keeps her bank account low, plays the game to get here "free ride". 

I actually am an attorney, and still send mine for extra vetting. 

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing. 

Post it on fb marketplace and boost the ad and I am sure you will get a million messages but don't make your ad sound like a motivated seller.

Making the next million is nice but doesn't motivate me to log long hours.

A pool can be a big liability, but can also be a bonus for the right tenant that is willing to pay extra for that amenity.

Oh also number one skill to develop regardless of the route you take is being able to identify and get in contact with motivated sellers.

Simultaneous to that, negotiate price reductions to the greatest extent possible because of this extra cost you are incurring.