At this time, 30 day rentals are legally allowed for any property in Kailua (unless the association has stricter rules), and I know some people who do quite well renting their SF homes on a 30 day basis.  

These forums are a great place to learn and meet people, whether you're just starting out or you're a seasoned investor.

Are there any hidden pitfalls or unexpected benefits I might have missed?

All sales of the property involved the same realtor, the same lawyer, all within 3 years.The realtor pretends to not have known about the restriction, the lawyer is sort of playing dumb but talking about mediating as I point out they missed the restriction that they themselves originally put in.

Is there anything I’m missing or anything I’m not thinking about?

Investing in real estate with your own money and from a position of financial strength is, I believe, a far more rewarding experience than leveraging other people's money and being dependent on a positive outcome to keep you afloat. 

Most of the people looking for arbitrage targets look for one-off Mom/Pop outfits that work off some lease they drew up in 10 minutes on Microsoft Word or a notepad, where subletting isn't explicitly prohibited.Because, again: if I have a property, and it can make more money STR than LTR, what sense does it make to give Broke Joe the keys when I can just make the money myself?

No offer write ups, no lender conversations, and if they miss the deadline, that is on them. 

Meanwhile I see people picking it up within days.What am I doing wrong?

I have noticed a trend over the pasts 10 years where more and more of the people have zero involvement in the day-to-day operations of the property and are only raising money.