Or of any alternative strategies to make this work?

You should have a good idea of every expense you have in your primary home, then add the STR specific:  (These are rough estimate numbers, depending on various factors)STR insurance - a special insurance that covers both the property and your liability, could be $2~4k in areas without natural disasters, could be more than $10k in some other areas.cleaning fee - approx. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

Is it better than your alternative uses for your money?

And alternating Fridays 11am-1pm. 

We are seeing big increases in HI because of the natural disasters in FL, CA, etc.

While California has long been a real estate powerhouse, Florida offers a compelling alternative with its own unique set of advantages.Let's spark some conversation!

I'd suggest that there is essentially no tax implication for this as compared to your alternatives.

I recommend homing in on what MOST vacationers are looking for in a specific market and try to find properties that have natural features/amenities that are scarce.  

The market will naturally balance itself. 

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