How do I know I'm ready to take the leap?

[Joshua Seguine]

Hello all, my name is Josh, I am new to real estate investing and I am looking to be a buy and hold kinda guy. I am interested in being a landlord starting off in residential and hoping to expand one day to commercial properties as well. I started this discussion to draw in the interest of everyone new and hopefully get more tips and tricks besides the beginners guide on everything and some real experience from others. I don't want the focus to be exactly what I want to achieve. Not everyone wants to be a landlord, some of you are just flipping homes. 

My worry is how do you now this property is "the one"? I feel like I have a lot of decent properties in my neck of the woods but as this is my first investment I am very weary on pulling the trigger in fear of getting the wrong one. Or maybe overlooking something better. If I buy the wrong rental is it easy to turn it to a flip? My worry is buying that wrong property or something is missed in that inspection and now I am looking at a major fix that might put me out of the market to be competitive rent wise. 

SO what I am looking for are those tips and tricks, the things to watch for when buying properties, maybe some of your good stories and the horror stories. How to know if your inspector is worth his salt. Me and my Ex wife's first property was a non invasive inspection, (didn't know that even existed) and we missed a crack in the foundation under the living room that took an effort to access through the crawl space.

Hope this makes sense and looking forward to hearing from everyone. 

Thank you!