I have read, watched and listened to most every piece of content I could find on this topic and I am just not seeing much downside and am seeing a TON of upside.

Cody Evans, I would find something that interests you, you tube it to death until you understand it and then go for it.

But if you change title, but not the loan, you should watch out for a due on sale clause

Also watch out for any HOA restrictions of course, and be aware that interest rates may be a lot higher for a non-warrantable condo - although I'm not sure how that would play out if it's your primary.  

It is important to always watch the market.

You need to watch the market yourself and get a real understanding of the market. 

They didn't have all the real estate books, blogs, YouTube gurus, financial calculators, etc.The best thing you can do is buy a house and educate yourself on how to manage it well.

What strategies have worked for you, and what should I watch out for?

I feel that I've watched enough videos and I am continuing to read.

There is no wrong way to do this unless you aren't doing it at all OR you're harrassing peopleIf you find yourself attending a bunch of educational webinars, watching too many tutorial/training videos, or anything other than those 2 things, take some time to stop and reflect.