Or would this raise red flags for conflict of interest? 

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

It’s true that you should be more diligent with vetting tenants - cash flow is great, but a destructive tenant can burn through it pretty easily and put you in the red.

Certainly not afraid of it -- the government red tape is Partly a question and difficulty removing a bad tenant is probably he biggest downside - that goes for any property though.   

And, if they had issues in the far past, it can still be a red flag too.

Anyway he made a video about the market being red today and then showed, very casually that his portfolio was up 24% on the same day!

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.

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

Sure enough the new owner was not renting their newly acquired property.Since rents have sharply escalated over the last few years, a rental with too low rent is a red flag of possible fraud.I sold a property in 2014, for $30,000 over 10 years ago.

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.