However, when you look at the Affordable Housing website, only 4 out of 32 available properties that accepts voucher are listed by $1,550 or more.Is that maybe a red flag that there's no demand for Section 8 in Cleveland? 

You can't purchase the software stand-alone (red flag for someone with some experience).

In my experience in foreign countries, there is often less consumer protections/ no central MLS or licensing/ greater risk to the principals, much more red tape, and overall higher transactions costs than here so it's important to look at the whole picture not just the commish %.

Even if you fail the first time (pretty much every inspection I've had the person finds something to flag) they don't cut off payment until they have come back out a second time.

Or would this raise red flags for conflict of interest? 

The fact that you can't get ahold of a landlord is a red flag.

I just find that they aren't worth it because of all the edits you have to make on the spreadsheet to get the same result, and one of the softwares refused to allow Journal Entries which seemed like a huge red flag to me. 

I just bought all the drywall, cement board, and a 3/4 full thing of red guard water proofing that I need for my entire bathroom remodel for no joke $110, that would have cost me $400+ at the store but someone else who already finished their bathroom just had a ton left over.

I can say while an eviction on a tenant’s record is a red flag, it doesn’t always mean they should be automatically disqualified.

If I buy this property and the money comes from someone else's account, will that raise any red flags within the IRS systems?