Dive in and learn all that you can. 

I have been reading and trying to talk myself into taking the dive to purchasing rental property.

You gotta run down the dock and just dive in head first .

Also I’ll say do a small job w a contractor first before diving into anything extensive.

I've read some articles and listened to some podcasts and I really want to just dive into something.

Meaning how deep would I go in debt to get that return?

I think younger generations are definitely willing and wanting to live closer to work and will go so far as to live in areas they might not have considered otherwise (Deep Ellum, Bishop Arts, Oak Cliff, etc.) as these areas become more appealing through investment. 

You dont need to dive right into the price discussion straight away.

You end up with really thick walls and deep window wells but this could be a much less expensive option than lifting the house. 

Getting your feet wet is invaluable, but obviously you don't want to go deep sea diving if you cant even swim yet.Ultimately I think it depends on your lifestyle, your personality, your risk tolerance/aversion, and your safety net.