@Joy Daniels I have one of my STRs in that market on Anna Maria and each “city” on that 7 mile island has different STR rules.

The 1031 exchange rule to defer your tax is two part 1) reinvest all your proceeds and 2) purchase a property (or properties / DSTs/TICs) with an equal or greater market value.  

If you go into A/B Class the rents are going to be too high to justify doing section 8, meaning market rents are higher than Section 8 is able to pay.If you go down to D Class areas you're going to attract terrible tenants and it will be a nightmare. 

But having those rules on paper was like carrying a big stick—great to wield when needed but mostly a deterrent.

A self-directed IRA could be a good way to defer taxes, but there are some rules to keep in mind—like keeping all the income in the IRA until retirement.

Consider the "2 of the last 5 year rule" to avoid capital gains.

Asking in the correct forum will get a better response.Read the RULES!

Focus on buying below market value, running numbers first (cash flow, 1% rule), and choosing a landlord-friendly location with job growth.

If the property is in a location that would justify these standards, then wait. 

A good rule of thumb is to have 3-6 months of expenses (mortgage, utilities, insurance, etc.) set aside per property for emergencies.