I've started looking for handyman referrals, you make a lot of good points.We currently use Cozy.com for listing, applications, and automated rent collection, and use SmartMove for background checks.

This is a  "Subject-to" transaction, hopefully using two notes.A seller is willing to take I/O for 20 years is probably 1 in a thousand and they will be taxed just as Greg is, make that 1 in 10,000.I'd bet Greg doesn't mention the other issues with a Sub-to, foreclosure, Greg can only foreclose on his interest, that could be paid off, the note to the first seller is pretty worthless, that can end up going to the state in a medical issue, then there are risks of bankruptcy, law suits by other parties, collections and servicing, deed transfers, insurance, liens and the list goes on, which is why you should not do long term subject-to deals.      

I don't want to collect any money from the tenant for the application since its a mess with returning it to them if we don't accept them.  

Used google voice last campaign and was not impressed.

http://nypost.com/2015/07/18/obama-has-been-collecting-personal-data-for-a-secret-race-database/

I also interviewed with a well known brokerage, but I got the impression that the  team leader I interviewed with was mostly interested that i would cap out on  my commissions and  I think she would have accepted anyone with no brains and a pulse.

I'm not sure if every collection attorney is as well organized as Linebarger law firm when it comes to maintaining those records.

., that dealt with all these rich people in Hollywood accused of homicide.I love how he scratched his head, using his hands, and using phrases likeoh, by the way…Can you explain that a little bit better for me because I don’t quite get that…I know that probably makes you sound stupid, but it allows the sellers to be disarmed.If you said something like,“You know Mr. seller the good thing is that if you rent this place out you will enjoy working with your tenants collecting the rents and all that, right?”

I am looking to get a multi-family unit that I could live out of and collect rent from so that I can truly start learning the ropes and what having a property with tenants truly entails.

This is where modification strategies come into play, that's why your collection skills and negotiation skills are crucial to your return.