When I read and I go over my plan it seems so easy to me and that I can do it, but once I go on MLS or zillow and All i Have is this picture and small description of the home, I get into this "paralysis by analysis" phase and everything gets all confusing then numbers start to scare me and then I just give up.

You may want to Google some pictures of the Miracle Method to see some before and afters.

Keep the pictures you took as evidence in case you have to go to court. 

We currently email them a paper application which they print, fill out, sign and text me a picture.

So I would say the big picture makes a big difference. 

Should I walk through and take pictures upon possession and have the tenant complete a move in checklist or is it too late for that now?

Simple before and after pictures of the property will suffice.  

@Jay Hinrichs for his vast knowledge bigger picture view of the world@Joe Splitrock for the post that I'm certain will save me from the disaster tenants if  it hasn't already@JD Martin perseverence, ethics@James Wise for reminding, reminding and reminding me more to watch out for savages@Michele and Bruce Fischer whose podcast inspired me to try affordable rentals@Scott Mac@Mindy Jensen an inspiration to women in real estate@Nicole Heasley@Bjorn Ahlblad @Russell Brazil@Brian Ploszay@Steve K@Marc Winters@Michael Ealy An inspiring story and huge inspiration to think BIGGER@Dennis M.

I am going to list them:TurboTenantIt is completely free to advertise your rental, screen your tenants.You upload your pictures, write a description and it posts to 20+ websites for freeTakes about 24-48 hours for leads to come in.Once you select a tenant, they pay for the background check, upload documents (paystubs, ID, W2) and it is all set to you.It even helps you build a lease after you select a tenant (there is a $30+ fee for the lease)My referral code (https://turbotenant.com/r/T3du... disclosure.

. :) You are right, shows like that don't show the whole picture, and people who do no research into how to properly invest in real estate wind up in a mess.But also for novices who might be reading this post, Trademark does volume...which is how they make their money.