A strategy I was considering was mass printing a letters and putting them in mailboxes of said properties, however, I’m sure there is a more sophisticated, way to handle this situation.

My thought is to create a Holding Company “Brand” that could be viewed as more sophisticated when purchasing other deals in the future?  

Sophisticated sponsors should be able to identify and disclose the specific variables that made past deals turn out the way they did.In particular, you should directly ask them whether they have ever lost investors’ money.

My wife and I don't consider ourselves the most sophisticated investors.

You seem like a more sophisticated investor who understands the question of the health of the general economic atmosphere.  

Hired non auto, machinery and equipment, terrorism...

Vacation rentals have entered the sophisticated and complex world of dynamic pricing. 

DCF is definitely the more sophisticated approach, there is a good model on adventuresincre.com

They are fairly sophisticated investment vehicles and are not really appropriate for most non-accreds, they focus on capital gains, which is more likely to be an issue for accredited individuals, which ultimately leads to an easier path to raising capital in larger chunks.  

Nonetheless, by joining their lower level program, students can "become sophisticated investors" and hence invest in deals offered by higher level students i.e. the syndicators.