And with that as a back drop I look at while 20 units x $150 = $3000/month in revenue, that's also 20 units that have something that can go wrong with them. 

I think what you are seeing are a few maples that are really tall in the backdrop.

Is there a direct connection or elegant way to do this?

Without any backdrop we can't answer your question. 

Others might be fine with taking risk, but least by doing this a person can get an idea of what might go wrong. e) Legal document analysis: it will usually take a few days to go through the legal document properly, as almost inevitably there are tons of gotchas that either have to be explained, or mitigated with a side letter.

But as @Mike Dymski elegantly put it, if you do proper due diligence (DD) and evaluate (a) the deal sponsor, (b) the market, and (c) the overall offering itself, and all of it fits your preset criteria, then you're making your decision to invest based on the calculated risk. 

It was “professionally” taken, as in I paid for the pictures (it was not a selfie or anything inappropriate), but it wasn’t me in a blazer with a plain backdrop behind me.

The 2nd example you gave is probably a more elegant solution in this particular case.

It’s a good backdrop to the business.

Hey Melinda, My parents did a good job raising me, and luckily, as my grandmother so elegantly used to put it "I wasn't born yesterday"Anyway, IMO - I've fended off about 3 separate cases where I believe this would have been the outcome.