Also, property values there don’t generally increase like they do in the US.Trying to apply US strategies in another country often doesn’t work.

I’m active duty Air Force and I moved to San Antonio about 18 months ago.Your strategy may need to switch to older homes in other parts of the city than around Ft Sam or looking at home appreciation over rent (sell instead of rent or look to convert to a STR).I recommend looking for a home in the southern part of San Antonio.

Fear of being in debt and taking on risk in general....can be greatly mitigated, if not completed eradicated, by having clear exit strategies planned in advance.

I think going with a turnkey strategy is a great option, since you are out of state.

I'm a Boston University college student, and I don't want to live in the dorms anymore, so I'm planning on using the rent-to-own strategy to find a place to stay as well as to use for househacking.

What's your thought about the ability to retain the customers and replace the main person? 

Take the time to understand the markets, explore different strategies, and build a solid foundation of knowledge. 

What strategies or tools do you seasoned landlords use to manage this kind of stress?

Learn how to calculate what a property will cash flow.If you are interested using the BRRRR strategy and haven't gone through the book already, I'd highly recommend listening to on Audible or reading the hardcopy of the book.

Am I just rationalizing a bad investment strategy here?