Quote from @Matt Smith:
Thanks Christian. We are always doing work when down there, or updating, cleaning, adding value, decorations, furniture, etc.
I'd say we spent ~40 days there last year, and worked at least 35 of the 40 days. The first part was after closing, we went down there to get it prepped to list on AirBNB/VRBO so we were doing stuff each day.
As far as rental nights, we rented about 100 nights last year (no discounts anywhere) and weren't even listed on STR platforms until May. And it's a beach property so obviously it was heavy bookings over the summer, solid in the fall and very little in the winter.
It sounds like you are good on avoiding 280A with your personal usage.
To get the benefit of taking your STR losses against your other ordinary income (and a cost seg would help to increase the loss), I think you want to make sure your average rental period equals 7 days or less, and that you meet material participation. I think you can meet this practically three ways,
1) you spend more than 500 qualified hours a year on the activity
2) you spend more than 100 qualified hours a year and no one else spends more hours
3) you are the only one who participates in the activity.
One wrinkle; you and your fiancé might (likely?) want to split the activity since you each need to file a tax return. I think this might create an issue with meeting the material participation. Did you have a plan for this?