I tend to get my ball rolling so I can get off my keester at this job and do something I have found I really enjoy.

Welcome Adam :)Enjoy

As for Chicago RE, I enjoy investing where I grew up at..Thanks for the welcome Don.

I enjoy what I do for a living and this opportunity has created financial stability.

Because of that and the lack of time to enjoy it, we haven't pushed very hard.

He truly enjoys what he does and takes pride on every transaction.

Managing your own holiday rental is great for experience and getting your feet wet, but as you acquire more properties you might notice it's becomin a full time job which eats away at your precious time (which could be spent hunting and orchestrating the next deal, or just enjoying life ;) - there are plenty of companies in Japan who can do that for you, top to bottom, from advertising through  management and all the way to complete subleasing (meaning, they pay you standard market long term rent or slightly higher, keep the place occupied, renovated and constantly cleaned etc - less yield if occupied all through the year, true, but also zero hassle and hands-on mgmt required).2.

I enjoyed my time in Korea.

I'd like to learn a bit more about real estate investing to see if it would be something I'd enjoy long term.

@Gabriel Garces happy to hear You are enjoying the journey brother.