I've owned, and rented, a Weirs condo, island property, and other "standard" rentals. With all due respect to Realtors, generally, if you need rental income to support your purchase, you can't afford it. If it is purely investment, seasonal is not the way to go. Better to buy a good investment and rent for a few weeks as a tenant for your own vacation.
The time to lease is when you have owned the property for a long term and you need a gap-filler until the next generation can afford to to take over and you can pass the place on.
An option we don't see here often: Lease a place for a few years and talk to the owner about an eventual buy-out.
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