Taking on extra regulatory risk anytime you buy in an HOA.

How is the regulatory landscape for STR around Orlando? 

The more regulations and harder it is for small landlords, the more it benefits those with sufficient capital to deal with all the problems and navigate the increasingly complex legal and regulatory landscape.Agreed with the OP that the heavy hand of government will continue to shape the housing market, as it always has.

Account Closed Here in California we typically do not use lawyers in our closings and the paperwork/regulatory burden is substantial and always seems to be changing.   

They would have called for sure as the regulatory environment in Washington was completely uncertain. 

's comment:Also a good PM will be better than you at filling vacancies, evaluating tenants, regulatory compliance, and handiwork.

ValuePenguin is a good source for the relative cost of insurance by state.Operational Costs - Costs like property taxes, insurance cost, state income taxes, regulatory costs (ex: time and cost to evict), inspections, rent control, etc., have a tremendous impact on your return.