Based on the 1% rule, this doesn’t seem to make sense.However, the city and area we live in retain property value because of the schools, community, and location.

I think you could split after sale for a non-taxable event, the total basis transferred in would be split across the two "new" properties.Calling @Dave Foster to give his insights here, lots going on in this one.

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

So outsourcing some degree of property mgmt would be a must... but the deal won't work paying a local property manager a large % of my revenue...Instead, I would set up my "boots on the ground" (cleaners, handyman), and would need an offshore virtual assistant to manage guests and coordination of my local team. 

First off, congrats on making it to your senior year—that's a huge achievement!

The latter will typically cost you more, as there are two sets of closing costs and the front side will pass their cost on to you, so you pay twice essentially.

Depending on what you're looking for, you can find a good mix of affordable properties, especially in the under $200K range.

Feel free to reach out and can give some recommendations on agents and PMs here in the market. 

How to calculate return on investment, cash-on-cash, cash-on-equity, capex, and more.

, if this needs to happen before you close on a home?