It may be a chance to get owner financing, but that alone is not a reason to get properties that are worth less than the mortgage. 

Maybe select the family with the highest income to reduce non-payment chances.

The VA doesn't have a particular time frame printed in any of their directives, but if you try to use your entitlement again, before 1 year, chances are they will look at you extra hard; you would need to have a pretty good reason (new family member, significant change in health, relocation to completely new area).  

I just takes a while and there are LOTS of folks now getting in the market so if you can get to the home owners before it comes to the courthouse, you have a much better chance of making money!  

In the space you are in, high debt, short time on job, and short credit history, your chances of your "speaking with lenders to get better rates" stand little to no chance of moving the needle.

I kind of don't want to run him off, so I am taking my time to offer, he seems to be in no hurry to sell, and has expressed the option of selling just one for now....My thought is if I aggressively pursue the owner financing, I know this will probably run off chances of traditional financing, if he's totally un interested.

zero chance of getting a fractional loan on a SFHBrilliant idea: looking in frisco, right?  

He is serious.The other son (Sam) wants at least a little money before losing any chances all together and his price is a smoking deal.

Improvements if there is a good chance to pay off.  

For example, if on a scale of 1-100 a bond is a 1, and angel investing in a risky start up (that has a 9/10 chance of failing, but if success you will 10X-100X your money) is a 99, the "risk adjusted return" is probably very similar.