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.

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. 

Yeah, we are restricted.

However, are there restrictions on this?

Your program sounds spot on, I like the "graduating" to less restrictive properties, but initial intake into the most tightly controlled home.The NIMBY factor is certainly an obstacle, but can be overcome with persistence (of legal action to enforce one's property rights, assuming one is in a correctly zoned area).something that could be added is work outreach program, as the ability to find work after recovery is obviously critical.

Regulated by the county of Riverside not the city, thus not subject to the restrictions.