Surprisingly, you tend to live harmoniously. 

Let you Money pay you.3 - How to design, and execute, a REI Business plan4 - How all three of the above work together, in harmony, to be one as follows -     a)  The Market tells you where to invest (this is to find the micro-markets)    b)  The Money tells you how (these are you strategies, which will be different for each market)    c)  The Plan tells you when to execute the strategy/market combinations

These things need to work in harmony.

But is there a way to extract that data in large quantity as opposed to one by one? 

It takes a strong conductor to direct all of these players and instruments in harmony.

If the 280 offer was a known quantity then maybe that confidence in closing was worth 30k to the seller. 

All of them working together in perfect harmony. 

Quality or quantity?

I get his position, too much potential head-ache with unknown quantity of new partner(s) and potentially less return for him, when he has spent a life time forming his own company/dream team and investor pool.

Here is a breakdown for simplicity:Fund - Pros are large quantity of assets = diversification and lower volatilty.