So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

I tried to create rapport with the owner over the phone but waited to present my real agenda only in person.   

I’m not a former IRS person.

Personally, I would hang on to the cash.  

Dumb question - but are these auctions online only, or in-person? 

Personally I like the Section 8 program when the property is located in a super poor area with a ton of blight and crime.

With a Conventional Loan you can buy a SFH, Duplex, Triplex or Quadplex with as little as 5% Down if it is your primary residence as long as you have the intention of occupying one of the units for 1 year after closing escrow.This is the strategy I have personally implemented and have assisted many of my investor clients in doing the same. 20% Down is also beneficial as it keeps your payment low but it does limit your ability of buying more real estate faster.i would be more than happy to discuss the different strategies with you over the phone or in person.

I would be fine with a $10k non-refundable retainer and $500/hr. personally.

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

The cost to repair your vehicle, and perhaps the other person's car, will be WAY MORE than the cost of the insurance premiums you saved by not having insurance.