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. 

Just from the little you wrote, it's pretty heavy on the red flags. 60 days on the market (depends where this is whether that is a lot or just fine, but definitely overpriced at this many days) plus no sold comps.

What’s the biggest red flag you watch for when vetting borrowers?

In my opinion, TXTing takes out more from you then actually bringing in - It often feels like a constant game of cat and mouse with phone carriers.

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

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

A $200,000 duplex might have identical rents in municipality “A” and municipality “B” but the property tax rates will vary, local regulations will dictate licensing requirements, labor rates will vary & the particular location will dictate insurance premiums since insurance carriers will weigh local replacement costs and whether the municipality is viewed as being a “plaintiff friendly” in arriving at insurance premiums.Better situated assets will attract better tenants.

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? 

Or would this raise red flags for conflict of interest? 

The problem is that you have to accept the dog but the insurance carriers do not cover bites from Pitbull's.