It a little tough for me guess. South Bend drill presses are more rare than lets say Delta Rockwells that to seem to fit the old drill press niche a little more. So a South Bend guy may have to have it. There's only one similar on ebay for $850.
I see a lot of Delta Rockwells run between $500-$900 asking price, but its not too difficult to find those for between $300-$500 with a little patience.
I like all sorts of old machines, and I think old lathes and mills are more sought after due the weight of old iron, the craftsmanship and quality into them. But old or antique drill presses are a bit of an oddity in that sense. They were way more basic. Small, non rotating tables, single levers to pull spindle down and such. The swiveling and tilting larger tables, triple lever arms just seem more convenient to me personally.
I will say I ran a delta rockwell, 3 phase, that had a super smooth spindle. . . so again hard to say. You could start an asking price a touch on high side, than lower if need be.
I think a good deal could be put towards personal taste if someone is building a shop with all old iron. But you may need to sit on it a bit to get your value of upgrades out, or let it go a lower rate to pull dollars out.
