That dude is smoking crack. Even a super clean, all original blackface won't go for more than $22-2500 these days and that's high. If he took a grand off (assuming the trannies and circuit are totally stock and the amp works flawlessly), that would still be high, but a lot more realistic.
You are not out of touch, it's about $1500 overpriced. I suppose it wouldn't be unusual to see a drip edge priced in the $1400 range, but I doubt it would actually sell for much more than $1250. You can still find blackface DR for $2k or less, and they are the only ones with collector status.
A quick look at completed listings on ebay revealed a 1965 clean DR that sold for $3100. A fairly decent 68 sold for $1600.
I have a 64 that's really clean that I would not part with for under $3000.
Rock n Roll history is not a top seller at the moment but it will come back.
That's not untypical of a standing BIN on ebay by a dealer. There's always some jackwagon with more money than brains that will grab ob of those at 2am when drinking. Not much different than the 'make me move' function on zillow. How bad do you want it?