J5… Be careful with anyone who stays a month… as we have warned on this forum before, in most states here in the US, that will move the vacation renter to month-to-month tenant status, with all the rights of that status. So if they didn’t want to leave, for example, you’d have to evict them through the regular legal channels. Google Airbnb Palm Springs squatter case and you will see what a nightmare that can become. If you really want to book the longer stay, tell them it’s 28 or 29 days and can be booked in blocks llike that so they don’t turn into a nightmare tenant. In some states, we have heard, this is only a 3-day stay before they acquire tenant rights! Be careful!
I also refuse to grant any discounts with longer term stays. You make more money turning it over, if you charge a cleaning fee. Sometimes the longer stays are people who can’t find regular housing and could be motivated to squat on you.
Beware also of negotiators… it’s a red flag to me and speaks to their character that they are negotiating. They don’t respect you right off the bat. Usually does not make for a good guest. If they try that on me, I decline them. There will always be other guests.
The male guest sounds fine to book. I wouldn’t be so sure about the female. What reason does she give you for staying so long? You have a right to ask.
Solo guests can be trouble too… partying, bringing strangers back, etc. Make sure they know your rules clearly before booking them. My rules state “Only your registered guests allowed on property or in the apartment.”