I bought 3 guns, a pair of Colt 1911s (different models) and a Browning Medalist for $2500. All three in superb condition. I'm told I have an immediate $1000 profit if I chose to list them on Gunbroker. Maybe......
If your friend already knows what a "98% gun" looks like, I bet he has an idea what they're worth. A package deal may save him the hassle of selling them individually, and be "enough" money that he isn't worried about the extra couple-hundred he might have got elsewhere. Cash in hand speaks volumes. But YOU have to do your homework. He has and will expect you to.
Model 27-2's are getting up into Colt Python numbers. Especially the 3.5" barrels. 19-3's are also the peak of S&W craftsmanship - their master gunsmiths were beginning to retire in droves, so these are the last of the really well made ones. So even they are going steep dollars.
Once I bought a near mint Chief's Special snubbie. I had gone to Gunbroker and checked the "completed" sales where there was even a single bid (a huge number have no bids, so you know they're overpriced!). By listing out the pristine guns and their "sold" values, I arrived at a top-end value. I deducted 10%, and that was my offer. He winced, but knew it was a good offer, and took it. It was a legitimate 99% gun. Coiler666, wherever you are, I ended up hating that gun but I'm hoping you're able to enjoy it! You got it for a tad over what I paid for it, and still got a bargain.
Do your homework. Have the cash in pocket - hand the man a wad of hundreds. Tell him that wad in his hand is your offer for both..... Se where that goes. He instinctively will not want to hand those bills back to you.... If he does, be fully prepared to walk. If you aren't prepared to walk, he knows you'll pay more....