Hi Eevewilliam and Eleros, Welcome
Eevewilliam, since you are from Malta, please be aware of this warning regarding travel to Portugal in the following coming days (14 days mandatory quarantine):
https://www.sef.pt/en/Pages/homepage.aspx
Eleros, I suggest you to get in touch with this danish couple that now live on Madeira. They went to live there because they are in love with this Island. Check out their videos on youtube and try to get in touch with them by using their latest videos, maybe they will answer your questions.
Stay Classy Vlog at Youtube:
https://youtube.com/c/JoenRudeFalsner
Regarding rentals, I have already posted some tips from the tenant's point of view. One of these days, I'll put a similar for the landlord, as well.
Kind Regards