Furthermore is claiming the rent as income on my tax return going to look suspicious?  

I'd also be suspicious about those references if you're supposed to screen on a Sunday -- the only eviction I ever had to do was a tenant I accepted who was "self-employed" and in hindsight I think her references were friends posing as former landlords.  

3 units for 2 months here sounds suspiciously like $4200.

However, his paranoia about having people in the condo without his presence, even with our trusted friend, seems suspicious to me.  

The other suddenly rented out.This was after 1 was on the market for over 5 months and the other was on the market for over a year.I can’t help being a bit suspicious about this.

I've had the most success being straight with people, explaining my personal motivations if they seem suspicious, and not insulting anyone's intelligence.  

I let the title company know this is my private loan which is a loan to myself with my money via a family member, same with my broker....also let him know so that there is nothing suspicious about it.     

I'm sure they just roll their eyes when they see a POF for the exact amount of the offer....if anything, it probably makes them more suspicious.  

A reputable HML will get points either at closing or roll them into the note.90% of ARV sounds suspicious...but that is only my opinion.

You are right, these people are suspicious.