I do not know him, but the path he is leading you is a difficult path    Note difficult does not imply impossible; there are people who are successful with S8 housing    In my area s8 is so undesirable that they write laws trying to make it challenging to not allow S8 tenants.  

One of the biggest challenges is keeping the bathroom as carefree as possible.

Challenges?

If you get dealt that character card, your primary challenge is that you need to replace a lot of income to get out of the rat race.

The only challenge is that I’d probably need to hire someone to manage it while I’m not there if I do an STR, right ?  

Owning a US passport is gold, overseas.The black motorcycle in the middle and the guy kind of facing it, is Marvin. 

Challenges?

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

As someone relatively young, obtaining a conventional loan has proven challenging for me.

Challenges?