Generally using a loan to make a down payment on another loan is not a good idea.

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. 

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

Prob losing approx $5-10k/month (on average)

On the other hand, a home equity loan gives you a lump sum with fixed payments, which is more predictable and great for one-time expenses like consolidating debt or buying a rental.

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.

According to our lease agreement, the lease "ends at 12:00 noon on Thursday, Oct. 31, 2024.

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.

Can you share the cost range you for the service, and also have anyone used legalzoom's service to create on you may want to look at Will Maker by Quicken.