If anyone has any experience on either end of a transaction like this i would be interested in hearing from you.

It sounds more like you want to do work for a short time and have success without knowing much.

Talking to people who’ve done deals in your market, both successful and unsuccessful, will give you invaluable insights and help you develop your niche.I know that’s a broad answer, but hopefully, it gives you a good starting point!

He’d likely play the role of buyer’s agent, contractor, and rental listing agent—something we successfully did last June.

While there are some markets I feel are so saturated it is near impossible to be successful in todays market (Orlando), in most competitive markets you can be successful if a) have reasonable expectations and b) do everything right (price, location, pro design, pro photos, etc etc). 

@Jackson Pudlo you'll have a better chance of success managing a unit right next door and learn a lot.Versus...Buying a rental in a few years that not near you.One of the biggest mistakes newbie investors make is not paying enough attention to their rentals because they are too busy with family & work.You really won't be able to ignore a rental next door to you!

i had a lot of success with direct mail and actually a fair amount with email. 

Most lay people have zero idea how to get through a transaction.

Many exaggerate their successes to get you to invest with them.

I will summarise my learnings to date and share a little about the process/rules I have developed here to hopefully be successful in REI in the Portuguese market.