We book 80-100 nights a year and have a very little tax bill, no utilities, low maintenance and no cleaners! 

Cleaner.

@William DavidsonI’m sorry to hear about your father.Using a LLC (or partnership) would be cleaner for splitting up the profit/losses every year and when it’s time to sell.

I recommend the cleaners we use and they want to use them which to me is a very good thing.

Sourcing cleaners and vendors look to be challenging though.I realize that those are not all on the UP, but they are in an overlooked part of the country for a lot of investors.As for WI, I have not looked closely anywhere other than Baraboo/Wisconsin Dells, which would get you close to those numbers the last time I looked.

I think part of this can be remedied by communicating with your cleaners to make sure they are spot checking all locations.I'm curious about your situation Karissa. 

She’d work during the day while we were either at school or daycare then come home to feed and bathe us before leaving for her night time job as a hotel cleaner.

I would try seeing if the sellers policies are assumable to make the policies a little cheaper for now.For Cleaners, ask your realtor and join the Galveston STR and real estate facebook groups… people in their advertise a lot!

That means spending $5 on grout cleaner and spending a few hours cleaning that perfectly good floor instead of ripping it out and replacing it, which will take years to recover the cost to do. 

Yes, there's always the "throw the job out on thumbtack, taskrabbit, etc" but that still has some overhead involved.If Turno had some feature to find a "handyman" for a task at a certain property EXACTLY like it does for finding a cleaner to clean a certain property...take my money!