@Bruce Woodruff I appreciate it! I'll definitely post my questions.
I think my biggest fear is basically blowing it and losing a bunch of money. Or netting so little it isn't worth the headache. Then I wonder how much capital I really need. I'm looking at properties that are $200k-$400k. I keep hearing that you shouldn't invest money that you can't afford to lose. Well it feels like I'd never be in that position. If I were, I wouldn't even need to invest. My financial upbringing was very conservative... do the job, do the 401(k), don't get risky. And REI is risky.
After that, I like to know as much in advance as possible... for example, a resort has condos for sale and housekeeping is part of the HOA fees, but what all does that include? Do I still want my own independent housekeeper to turn over the property in between guests? Etc., etc.
But as far as info goes, I DIY, so I have an OK handle on houses. Whenever I do something new, I find contractors on YouTube and watch their videos on repeat and take notes. I worked for a real estate agent for about 18 months, but I didn't get into how the deals were structured. I did some of the paperwork, but most of what I did was marketing. None of that "feels" like enough knowledge.