You understand some of the basic concepts, but also have some giant holes in your plan.

I'm 42 with a wife and two kids.

Think basic, durable furniture that looks good but can withstand college life.4.

Hard to give good advice without more info, but since You are single no kids it's hard to beat buying a single family fixer upper and living in it for two years and then selling for tax free profits....I'm a big fan of Waltham these days $.02 

Set up a basic system to manage your listing, update it monthly, and always ask guests for feedback—and don’t forget to casually ask for that 5-star review!

That is to basically keep you honest, so they judge can tell you tried.

What a great find, though - a single family turned into basically three streams of income, assuming you get an ADU permitted!

Once you know the "basics', you can then invest OOS more successfully.If you can't afford to invest in your home area, how will you grow your knowledge of an OOS if you take a shotgun approach to where you buy?

DFW Real Estate Investor Club.I think both are about $20 per event to attend the basic meetings. 

Courses and webinars are great if you're getting basic information to help start you off, but you'll never truly retain the information if you don't apply it.