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I had a cottage on Lake Michigan, in Michigan within 2 hours drive of Chicago, for years that I rented out on a weekly basis through a management company. It was easy and painless. I would own another "vacation" property again since you aren't dealing with the heartache that accompanies long term renters. It's pretty rare that you get people trashing a vacation rental, especially if you choose wisely and pick a "family" destination and not a party destination. This was pretty lucrative for us, even with the property company's cut, and since we loved the area we always reserved weeks for our own usage, and our family's usage, and it was a win-win all around.
I also have a farmhouse that we rented out for years as well and did everything from placing the ads to collecting the rent and making repairs. That's been hell with the heartache stories of down-on-their-luck renters, chasing people down for money, damage (!), and just the way some people live - oh my Gawd disgusting. The absolute worst have been the self-professed Christians in my experience, with the apex of bad being a Baptist minister and his family who rented from us for 6 months while the parish house was renovated. They knew we were atheists by the time they left (yes, actively tried to "witness" to us over and over). In indelible ink, they scrawled Bible verses about repenting of sinners etc. all over the living room walls before they left. Not even Killz got it out, I had to re-drywall the entire living room! I will never, ever, ever, ever (did I say never?) do long term rentals again.
We're now in the process of renovating the farmhouse to live in ourselves and I am soooooooooo relieved to be out of the rental business.
YMMV. It can certainly be a wise investment choice. I know we wouldn't be in the financial place that we're in without investing in real estate (we're not rich but certainly not in terrible shape) - the market is pretty weird right now but the bargains - wow! Good luck.
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