Hi @Jacob Temple, The tax code and regulations do not have any "holding period" required. 

Also, be sure to check local rules and regulations, it seems like Hawaii isn't very friendly to STRs overall. 

Look at the u regulated TX Power and also home construction standards.

You need to understand the Florida ADU regulations.

Also check local regulations.

See Treasury Regulation 1.48-12(b)(2).If the rehabilitation is completed in phases, the same rules apply, except that instead of a 24-month period, a 60-month period is substituted.

However, there are (were) a number of new regulations and restrictions on short term rentals which dissuaded us from investing in the market. 

And regulations are never ending.

VA loans also have more regulations and inspections than conventional loans. 

There are many best practices and many aspects that can make a SFR a good house hack, but here are a couple thoughts:When researching various areas in the Atlanta area, you'll want to become familiar with local regulations regarding tenant laws.