I'm up to date on Portugal's various STR restrictions.  

One other thought is fully furnished mid term rentals.. these have worked very good for us in Vegas we get a double or better rent premium on ours.. much less work than STR and you dont have to worry about ordinances or HOA restricting them..

They promise 100% financing, but their lending criteria are incredibly restrictive.

I live in Tahoe and there are multiple restrictions on STRs so if that is in the plan check the local regulations. 

Look for an existing one that has the cashflow.No deed restricted community.

They care about eating all the pie by themselves and sharing it with those who finance their campaigns and free vacations, that's what those law makers really care about.

Denver just loosened most of their restrictions around ADU's also but they still have to have a foundation.  

Generally speaking, month to month doesn't make a lot of sense to offer, especially when "no cause evictions" are prevented or restricted.

Apparently you can do it with a "Crédito Multifunções" but there are some restrictions implemented by the Bank of Portugal: If the property was acquired less than 2y ago: This type of loan is limited to 80%-Loan To Cost (from what I understood rehab costs are not included).If the property was acquired more than 2y ago: This type of loan can be used until a max of 80%-Loan to value not limited to the acquisition cost.Let me know if you had different feedback. 

I believe in Florida, HOA liens have priority as of the recording of the declaration of the restrictions except for first mortgages where the lien has priority as of the recording of the lien.