ID like to chip in with a couple of comments. The Canedy -Otto drill press looks like it is in very nice condition. Maybe the second best looking drill press of this size and vintage I've seen. Prices vary on these around the country, but easily should go between $250 and $1100. At the high end these machines usually stay for sale a long while. This DP looks like it has power down feed - which is very desirable for drilling through large steel work with 1" and larger bits. If you check out the drill chuck probably you will find the make and size it opens to. Maybe a "1/2" chuck if it is modern and small, or possibly up to 2" chuck - considering your dad and Grandad's original professional use. Does it have any drills with it? It so, that would be an added selling point. Also take a look at the motor and publish what horsepower and power rating ( 220volts maybe). also whether three phase or single phase power. These things will help sell the machine for a fair price, and let prospective buyers know what capability the machine offers.
Regarding your lathe - that is a fabulous old South bend late - I've never seen one with the particular gear change box / data plate yours displays. This certainly is a 1920's maybe earlier vintage machine. And it may be a collector's item, hence worth more than usual if the ways still have little scallop like scrap marks showing. These lathes were hand scraped to be perfectly flat and the scrape marks are designed to retain way oil - lubrication to prevent the machines surfaces from wearing each other out of true. Take some oil and a rag and clean up the ways a bit under the chuck. If they still show small circular stirations, then you may really have something!
The catalog number relates to the year made. Over on Vintage tools web site you should be able to find a listing of early day SB lathes, by catalog number. That should help you date the machine. It won't be the same physical build as the more popular, and more common Ww II SB 9" lathes. But this one looks like it could be a real keeper!
Edit: As FYI, your lathe appears to have the original 'Japaning' finish - same as Henry Ford applied to his early day Model T's " you can have any color you like, as long as it is black." Japaning was made by melting a mineral known as Gilsonite or mineralized asphaltium, then thinning with turpentine and linseed oil then adding 3% lamp black to produce a liquid finish. This was baked onto the lathe at 400 degrees until dried, then repeated three times to build the coat. Stuff lasts forever and protects the underlying iron/steel from rust remarkably well. It also dates the lathe to pre 1925 or so.
If your prospective buyer doesn't want the wall mounted drive assembly currently with the lathe, please let me know. (Many people upgrade these drive systems with a newer style SB 9 motor mount. My lathe, similar vintage, does not have this drive assembly and I would like to restore it to original condition with these brackets and drive line. Previous owner inexplictly threw the back gear assembly away! They aren't available anywhere now, as they have very little utility- except to mate up with these early day machines. Thanks much!
Regards
Glenn B.