His practice covers the state of Florida...

Not only is this good practice, but over time you will earn their respect, which means you will earn their investment funds.

You are subject to HOA (be careful here), town regulation, and neighbors.

But if your neighborhood has lots of garage conversions, then that would lead me to believe you don't need that garage and that it's normal practice to convert the garage.  

My guess is there is a due on sale clause.Now you broker may be speaking from a practical sense, knowing the risks is minuscule (for both issues) so he glosses over them.

By leveraging cost segregation and the Tangible Property Regulations (TPR) of 2014, you will substantially increase your cash-flow. 

Once you narrow down your preferred markets for purchase, hire a knowledgeable realtor who understands the STR regulations and the "sweet spot" of each market. 

Although technically possible, it is my understanding that the practice is frowned upon. 

Look at repair and deduct or rent withholding regulations for your state. 

I'm at the point where at least I know it's doable with zoning and permitting, given I modify the eaves and meet the regulations for exterior wall protection.Offshore architect still working on the floorplan, but conceptually this is what I've decided on.To be honest, I haven't gotten to looking into SDCs, thank you for your tips I will get on the worksheets to figure it out.Boxabl seems like the most simple solution, but I'm fine learning these skills that I might have a change to use in the future.