Trust is something that deep down you know you have with your family members. If you have any indication that anyone may try to act in their own self-interest at some point then it’s probably not worth owning a vacation home together.
This may sound simple but it is so important. You must sit down with all family members to ensure everyone is on the same page.
It only takes a few minutes to set up a google calendar that everyone in your family can access. I can’t tell you how helpful this has been. At any time I can check the google calendar to see what weekends are available or already taken.
The best way we’ve found to do this is by having a checklist. This is helpful for all of us and even more so in cases where we rent the place out. The arrival checklist includes items such as how to turn on the water, hot water heater, and ice maker.
The money we pay into the vacation home fund every month covers the obvious things like the mortgage and HOA fees, but what about unexpected expenses? We each put into our account more than necessary to plan for these expenses.