I'm quite familiar with real estate but new to the investing side. I'm reading several books including rich dad poor dad, how to invest in real estate and a couple others, watching youtube videos, and exploring this website. How long does it take to be comfortable or ready to start investing?
Only you can know how long, @Dominique M. Conwell . It all depends on how much time you're investing, your base level of comfort coming into the process, and what your ultimate goals are.
I think you need to be comfortable enough to quickly analyze a property and understand where the blind spots are. I.e. you know what you don't know and minimize surprises. I recommend analyzing 5+ properties a day. Before long you'll be able to do it in your sleep (and probably start having dreams about Cap Rates and IRR!).