Without experience I'm worried there would be a tendency to either underestimate repairs causing a large gap between what the seller already accepted and what realistically you could offer after having a contractor have a looksie or overestimating and losing the deal entirely. 

When (wholesaler A) brings a buy-hold deal, light repairs, with equity at end, 2k deposit non-refundable, 20 day close contract, to  (Investor, & licensed Realtor B) and B doesn't want to buy it at that moment, but sees deal value, has 100% all cash buyer in hand who would most likely want deal and will title and close, what are "B" 's options to put some modest coin in his/her pocket and make the deal move forward fast?

Not so great contractors can have a tendency to shed company names (assuming they set one up originally), so this is one way to check that.

The disclosure from the seller scares me though, not knowing your state laws, there's always a tendency that it will pass along to you, the best solution for me is to email title company/attorney about the situation, that way if they say something, you have it on record, over the phone conversation falls down on he said she said, while email transcripts are admissible in court.

Monthly payment plus bonus at end of the period?

I had 4 people come out to look at the roof, one being third party who owed my realtor a favor, and every one of them said the roof was at end of life and had hail damage.

I have a tendency to analyze problems to death... so that's going to be my biggest challenge. 

oh ok. i would call someone local you know and ask if they think its same price. at end of day if its inspected, passed and same warranty might not be worth fighting

My choices at the time was 20%,25%,30% down-payment & 10yr, 15yr at most otherwise it was a 5 or 7yr arm with balloon payment at end & rates started 2 to 3% on top of PRIME rate plus points for the lower rates.

For example desert areas have a tendency to require asphalt roofs to be replaced much more quickly because of the wear and tear on them from the heat.