What kind of returns do they expect to take from a 50k initial investment?

You may run into issues trying to take a HELOC out on an investment property, and even if you can I doubt you'd want to use it for a down payment for a primary because the rates are much higher.What kind of cash flow would you be generating from your multi once you move out?

One of those goals is what kind of returns you want from your investments.

The problem is I Don't know what kind of contractor is nessary or if it's multiple contractors.

Seller's response: He said, "Yes, I have heard of a land contract, but I’m kind of hesitant because I know some locals who land contracted their assets and ended up with a distressed property after a few years.

I think this is kind of a daisy chain from other sources, so it's not worth it; it's a kind of like Investor Lift for wholesalers.

If you can handle that kind of discomfort, I'd recommend moving to an emerging market and house-hacking (that's what I did).

I suggest finding a local AirBnB investor who can guide you on the prices in your area and help you decide what kind of units are suitable for short term rentals. 

Also given the fact that its darn near impossible to get any kind of civil judgement executed and collected on in Portugal. 

What kind of loan did you use?