If your already in a high tax bracket, then the commission will be taxed at that rate which may be more than the capital gains.

As in, is there a tax loophole here to avoid capital gains?

Similarly, there's a divide on whether taxes should be included or not in determining NOI.This lack of consensus has left me scratching my head.

However, i know that there are many cities within California that prohibit or heavily tax Airbnb's.

Good choice :)Being able to start a journey of deferring that tax will compound for you as long as you keep the new properties or do a 1031 whenever you sell one. 

Also, if you are given 3 weeks before bids are due, that would be a good time to check property-tax and other publicly available information, rather than trying to fade you bid after you've tied up the assets for a month. 

I would love to see the numbers: mortgage, insurance, taxes, rent.

On the other hand, a SFH is generally farther from the water (I'm trying to stay within golf cart distance to the beach), has less amenities than a condo, and higher property taxes, but seems like it would offer more appreciation than a condo.

The associated costs, such as increased insurance and property tax, could pose a challenge under this model as well.

Or you have to make some lifestyle changes to take full advantage of it (e.g. real estate professional tax status).