The “owners unit” occupies the 3rd and 4th floor and we would rent out the other three units, one of them being commercial.

Hi @Nina Erlandson, yes we just had our last one last Wednesday and we were talking about the new Spanish housing law in Spain (nueva ley de la vivienda). 

If this is the case, should I start of with a condo or SFH and house hack. 2.

The relationship is between the HOA and you (the homeowner), so the fee is levied against the owner of the house.

I work with first timers that are house hacking. 

Literally maybe 3 month old article and really contradicts a lot of what you said:https://www.benoitproperties.com/news/miami-housing-market-s...

We currently own the original property in our personal names since it was a house-hack.

Thanks for the info, and I would think a prospective seller would likely hesitate to use a listing agent that is unable to list their house on the MLS.I read that some virtual brokerages will allow you to join them without being a Realtor and list properties on MLS through them.

I've interviewed the owner of the company and he is a real estate investor himself and clearly knows what he's doing. 

Short Term Rental - This is the permit you would apply for when pursuing a non-owner-occupied STR in the R-1, R-2, R-3, RSL, RSM, PR, OS-1 and OS zones.