My skin is crawling just from seeing it.

It would be nice if all listings (via MLS or fsbo) received a fair shake with agents, but true that not all listings are created equal and no doubt implicit bias comes into play for all parties.

I get that there might not be any way to really 'know' when I'm ready, but the more I read/listen/learn, there does seem to be a pattern of fairly common problems people run across, or steps that they have to take.My current goal is to try to buy my first rental property before my next birthday in May.

If you value a good relationship, like a good friend, I would communicate this concern with them and work out something that truly is fair to each of you. 

But they said they still have fleas.At this point, I feel like it is fairly safe to say that they brought the fleas in with them or at least their cleaning habits (or lack thereof) have contributed to the problem.Anyway, my question is who is ultimately responsible in this case? 

I know this isn't exactly what you're looking for, but for folks scrolling by, I have found rentometer.com to be fairly accurate for rent prices in Connecticut. 

My personal residence is fairly close to there and I would love to invest in that neighborhood.

The forums tend to be fairly practical, so you can pick up some real world info pretty quickly.

I have a fairly strong understanding of the ramifications of the point of sale inspection process based on my buying/selling a few times in my greater Cleveland suburb. 

If you haven't already done, you might want to check out this site to see what Section 8 consider and will pay as fair market rate.https://www.huduser.gov/portal/datasets/fmr/fmrs/F...Also, you want to find out who your local housing authority is (cha.org) if the property is located in Chicago.