Jay,
DT/SW models do come up for sale from time to time, but they fetch a fair bit of money as they are one of the more sought after prewar Douglas models. There were a few sold at the Bohnam’s auction at the Stafford Show, Oct 2007 (results via their website.) And there is usually about one per year that turns up on eBay.
Mike Smith (now deceased) had one of Fay Taylour’s 1929 DTs is doing the rounds at the American AMCA meets for about $30K. I believe his sons are continuing on with the business of buying and selling old motorcycles and related parts. However you will need to ask around for contact details.
But it could well take several years keeping an eye peeled to find the 'right' bike in the condition and price range you want.
Two of Reggie Pink’s machines are known to be extent. A 750cc converted for hill climb is currently undergoing restoration in New York. Another 500cc in more or less standard trim is in Pennsylvania, and has been for sale on again, off again for the last twenty years. Last time I heard it was not for sale and the owner was going to restore it.
Keep in mind most DT/SW engines will have knackered lower ends, which will cost a fair bit of money to put right. It is the nature of their design that you can not replace the crankpins or regrind the existing ones. (See link
here for pictorial guide to the prewar OHV lower end.) Replacement is the only option, which will set you back another $4k if you can get the bits. New connecting rods are available, but the latest batch of new crankshafts is sold out. The next batch would require an advance order of some twenty units, which no one is keen to bankroll! An alternate design is under consideration that would make smaller batches feasible, but the reality is those would be several years away.
The rest of the engine and chassis is fairly conventional, so the usually inspections and tire kicking applies.
-Doug