Once ever few months I pay them $125-150 for a "deep clean"

I don't care how much insurance your tenant has...you will be seen as 'Deep Pockets' guy

I paid for the clean out and a deep cleaning of the home.

An investor will look at 100 deals before one is worth taking a deep dive underwriting.

A good realtor should be proactive, knowledgeable, and easy to communicate with.Do they have a deep understanding of the market?

It was about 20 feet down in the front yard, so that's  a pretty deep trench and someone had to go down there and clean out 3 weeks of tenant solids before they were able to replace it with PVC.

Again, if you have deep pockets you can just buy a portfolio. 

Class A property RentReadys rarely exceed ne month of rent, many only need a deep clean.Class B RentReady usually requires about one month of rent in prep.Class C is a crapshoot.

Track record…I like that they’ve been in business for a while, but I’m not as comfortable with their history in industrial (maybe I didn’t dig deep enough).

I don't have answers for all your questions but my opinion will be as long as you disclose to the sellers and they understand that they are selling their asset in a deep discount ( in your case $18500 vs $60K value) you are fine.