In my experience in the Tampa market it is very hard to find a new construction in a new development neighborhood that will cash flow positively after a CDD, HOA, higher RE Taxes and then all the other expenses associated with owning an income producing property.

Is setting up a HOA difficult/expensive/annoying for example? 

@Kettly Soivilien the biggest thing would be finding out what rules and regulations the HOA has in regards to short/long term rentals.

The HOA dues often kill the returns.1st get prequalified for a loan....see if the payment and HOA dues, taxes, insurance fit your budget.Then go shopping....is the style, location, price a good fit for you?   

If I'm buying a stand-alone single-family home for myself, that isn't part of an HOA, is this still true? 

I touched base with the HOA president who acknowledged the smell in the elevator but has no inclination to do anything about it.  

In almost all states the mtg certainly survives the HOA foreclosure.

Many HOAs/gated communities have restrictions on rentals. 

And then there's HOA and city regulations etc.

Also check the HOA fees and what they include.