Welcome to Airbnb!
I would advise to step back from this one. You are discovering problems and do not yet have much experience with Airbnb, so do not rush into anything.
While your guest may be very nice, she is an expert and you are fresh meat, so you are correct to be wary.
As a long term landlord of 30 years, I brought my own baggage . Due to my bad marketing, I took whatever came and was grateful.
I stressed about scheduling and filling up weekdays and single days.
Wow! Airbnb is SOOO different than my long term landlord experience. Because they market world wide, you'll have alot of opportunity to rent in the summer and fill your calendar. Airbnb can even rent your single weekdays!
If you really like this guest, make sure you change to a STRICT booking setting. At least you'll get one month's heads up.