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So whats the question then? What do you want the property for more? Money or easy vacations? Some management firms might black out dates that you want to use. Like you said, some limit you to a certain amount of days a year which seems kind of ridiculous considering you still own the property (unlike a time share).
Like brokencycle said, a good management company is worth seeking out.
We spent a couple weeks in late May/early June at the Ritz in Waikiki and that's what is happening there. It's all on the "residence" model, so the suites are sold to owners, then the Ritz rents the suites out as hotel rooms.
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Hard to tell the difference between the high rise conco and a hotel but with a mix of actual residents and visitors.
The last couple of pages make me realise I live in a slightly different world than some of the rest of you. My idea of a great holiday usually involves a canoe and a tent...
Then why not just continue to rent there? Its not really an investment if you aren't going to get a return and it seems costly to only go 30 days out of the year.
We are if the mind to never buy anything other than our primary dwelling. We've multiple friends with vacation properties and it seems to become more a chore than anything else as they feel committed to spending most of their vacation time there. Each to his own but for us no commitments.
How much of the place can you lock off?
Seems pretty common in vacation rentals I have been in that there is at least one closet/storage room with a lock on it for the owner's stuff. Maybe an additional shed or similar for the owner's own toys at a beachfront place.
Wonder if you could get something like a 2-3 bed, 2-bath place and then just lock off the master suite and rent it as a smaller unit. Could also lock up a kitchen cabinet or similar if you want to have nicer cookware, liquor, etc. available to yourself.
Then you can keep it "yours" in the private spaces but still derive rental income. Keep a wardrobe there, keep your toiletries in place, etc. Gives you much of the ownership experience where you don't even really have to pack anything, just show up, unlock the door, and enjoy.
Unlike just buying a small place, you've still got space for guests...and in my experience, that's a big part of a vacation property: Being able to invite friends and family to join you at the place. That's the one place where it really starts to feel different from just going and renting a place. Especially if you are in a fortunate position compared to others...you can let people stay for free without the weird awkward baggage people might have if you instead said "Lets go rent a beach house, don't worry, I'll pay for it"