I live in the Greater Boston area.

However, what will you do when there's a problem with one of your units and you live an hour and a half away? 

I realized I needed to find a way to earn a living while also having the ability to live the life I want.

Hi guys,My Mexican wife and I (Australian) live and work in China as international teachers.

Still, I'm concerned about potential tax complications given the property's location in Maui, my residence in California, and my in-laws living in Washington.Am I overlooking anything crucial here?

What subject to invokes is entrepreneurial risk; the thing all real estate investors live with in an attempt to grow our assets, and gain a financial “free” lifestyle.  

I have documentation of payments and evidence he lives here and a rental agreement.

NY isn't TN so you need to do your research and check the comps.If you acquire it, you'd have an option to flip it, develop it or live on it.  

I'm currently living in Boston, but plan on moving back to the Pittsburgh area in the next month.

While your immediate position doesn't change, you now own a property with 200k of currently inaccessible equity.Also with your first one, if you can put down 5% or equally low, occupy it, and do a live-in flip, you may not have to refi; save up for another 5%, do it again, new primary loan, etc.