Stop expecting your siblings to suck less.
Dear Prudence,
I am the oldest of five and the only one with a good job. I’m married, and my husband has a successful career too. While we are a close-knit family, this financial disparity has created resentments on all sides. My siblings have variously struggled to find careers. They are all self-sufficient but live paycheck-to-paycheck and are open about their financial struggles. This translates into an expectation that I pay far more than my share of group costs and that I pick up the tab for dinners. I don’t mind treating my family sometimes, but I hate the expectation. I hate the dinner-table “joking” that since I have a savings account, I can pay the dinner tab. I even buy my kids’ birthday presents on behalf of their aunts and uncles but never get the promised reimbursement.
I am now considering buying our parents’ vacation cabin to give my parents liquid funds and allow my parents a few more summers up there. I also want my kids to experience the joy of the mountains I had. But I am filled with dread knowing I’ll be bombarded with requests to use it (for free) for weekends with friends, etc. I had planned to rent the cabin out most weeks to recoup some of the costs. I sometimes want to scream: “While you spent your 20s flitting from job to job, taking months off to travel, and buying luxury goods, I was eating ramen in grad school and socking away every dime to pay down debt! We made different choices! I love you all, but it is not my job to pay your tab or provide you with free vacations. You’re adults!” I need to figure out how to draw boundaries without ruining these relationships. Am I being a miser?
—Siblings’ Bank
Re: Stop expecting your siblings to suck less.
"The cabin's rented for X weeks and is open at Y time. To cover my costs please venmo me $Z and then I can send you the access info."
Expect that they won't like the terms and expect that they'll want to get in for free. But no one can take advantage of you if you don't let them. So put teeth in the plans.
Anyway, I think LW just has to use their words. As a compromise, I would pick a time slot (say 2 weeks in the summer) for family use. Tell everyone they can come and go for free during that time. Any other use would need to be rented through X management company.
As for the vacation cabin if they chose to purchase it, I think they can nip a lot of this in the bud right from the start. I'd send an e-mail to everyone right after the closing...ie, written documentation that can be referred back to at any time...about the new terms. Including verbiage that they have gone to great expense to keep this cabin in the family but, to help them do that, it will need to be a vacation rental the majority of the year.
If the LW doesn't mind disclosing this, I'd even include the "black and white" numbers of just how much this cabin costs on a monthly basis. Mortgage/insurance/taxes/vacancy/estimated maintenance/property management. All of it. I wouldn't be surprised if that "monthly profit" is a RED number and more like a "monthly cost".
A rental, especially a vacation rental, is a far cry expenses-wise from owning a personal home. Most people have little idea. Which includes the siblings and **cough, cough** possibly even the LW. Who, of all people, should be crunching those numbers hard to know exactly what they are getting into. Without the info about cost, their siblings are only going to be picturing the gross revenue that the LW is just "raking in" from being so greedy and not letting the rest of the family stay there for free whenever they want.
Serious question, I want to know how LW grew up.
I genuinely ask because with my mum and her brothers, they grew up going without often - so the ones who may not have a job, just do without if need be.
Say something to your siblings to stop the jokes: "We don't find comments about comparative net worth funny, and they stop being made or we stop hosting you."
Also be firm about the use of the cabin: "The cabin is available from X to Y dates. We will need a deposit from you of $X, your signature on our rental contract and your respecting these rules. Yes, just like Airbnb."