Hoping to learn more about areas you like, the market specific hurdles you’ve encountered and anything else that you like to share would be super appreciated!

The whole credit score thing is such a scam.

I was nearly scammed by a seller in the US who I met in person, met his "associates", toured the property with and everything, but my tip off to do more research was that he was against using a third party to hold funds in escrow even when I said I would personally pay all associated fees and noted that it would not delay closing at all. 

The problem you're going to encounter is your income is not stable, and you just started doing it. 

Maybe you had a different experience than what many investors are encountering.  

Specifically, I’m interested in knowing:- What are the biggest challenges you encounter in property management?

Sorry to hear this.I would always say that "There is nothing wrong with any property as long as the price is right".Granted, some are not salvageable and the deal doesn't make sense even if the seller paid to me to take it lolOver the past 10 years I have witnessed many investors trying to do the same thing as you.Purchase from afar without buying turnkey and trying to do it themselves.This has been popular especially the last few years.Not many succeed unfortunately or they don't succeed in my eyes as they are into deals for much more than what they should be.There is a big trend going on where folks are made to "feel involved" with the purchase, rehab and property management process.The properties look great and off-course they do as rehabs cost $40,000 - $50,000.It doesn't sound like a lot of money for folks from CA and NY but for our local standards it is and IMO kills the cashflow and is unnecessary overcapitalization.Each to their own I guess.Just had a call the other week with a fellow from CA that bought a few turd properties from a local scam artist and is flying to town to try and rehab them himself.Another fella I managed to save even tho he lost his deposit of $1,000 as the seller (Another known scam artist) made him commit to the deal without allowing an inspection or even a walkthrough...If that isn't a red flag then I don't know what is 🤷‍♂️Hat's off to you for flying into to town to see the property for yourself.Wishing you much success

My wife and I first encountered VestRight and loved the sales pitch but also felt hesitant with onboarding/sales techniques.

Someone tried to scam me on here, asking to do business with him and lend him money in a double close. 

I'm certain similar listings exist throughout the Caribbean, that's just the first time I'd encountered it.