I guess one can rationalize anything if their views somehow put a few bucks in their pocket.

I think that buy-and-hold projects have less project-specific risk than a fix/flip project does and thus rationally carries a lower return.

They may rationalize a deal differently.Submit the offer confidently and don't be afraid to walk away.  

I've been following him for about 4ish years, and I think a lot of his ideas are rational.

Pro-rations have to be done etc...but my question is will I have a problem come the 1st when it's time to collect the current tenants rent $?

"Hope" isn't a plan, it's a rationalization for a bad deal, and is the most expensive word in the REI vocabulary.This is a cut and run...fight another day.  

Of course, my rationalization above doesn't take into account the location.  

Once you get emotionally attached it is hard to make rational decisions.

If you are buying a DST with a higher debt ration then you would need to buy a higher % interest in the DST to burn up your cash proceeds.There is no requirement to carry or replace debt just because it is a 1031 exchange.  

The relationship is much more important in CRE that residential but they have more ways to analyze & rationalize a deal.