Sapphire is much more of a vacation home community.The deciding factor for me was that Sapphire and Cashiers don't have a lot to do, except for golf and hiking.

The factors you mentioned are very important to keep in mind for any investment, but I like investing in areas I know. 

There are more factors than just the community (#beds, level of theming, location to the amenities, style of home (single family, townhome, condo) and others) But I would strongly advise to stay within some of the same communities you mentioned like Storey Lake, Windsor Hills, Championsgate and a few others if cash flow is your goal.

The major factor to standing out in any market is design.

It’s generally better to pay taxes, especially if it’s preferential LTCG treatment and make a sound investment with cash that remains than defer and make poor investment decisions. 

@Jon LaBorde An estimate like that is going to be useless for you because it depends on so many factors.

I mean by safest is on the volatility, for example STRs have many different factors, seasons of the year, local government regs and much more.

@Alex Messner, your decision, amongst other factors, mainly depends on you and your wife's financial profile. 

Look at factors like proximity to jobs, schools, transportation hubs, etc.

That’s a huge advantage.Totally agree on property management being a make-or-break factor.