DP's are pretty basic. For the money, i think the best values out there are used ones, as long as they haven't been abused or left to rust in a damp basement. If you're at all mechanical, even 80 year old machines generally require little work over what would be obvious damage. If you can find an old Atlas, Craftsman, Boise Crane, Buffalo, Delta, Duro, South Bend, Canedy Otto, Walker Turner or something similar that appears complete and functional, you might do very well. The usual work includes replacing bearings (some of the old Deltas can be tricky to find, but they're out there - Walker Turner too) in both the DP and the motor, replacing the electrical cord, new belt, and maybe a paint job. Sometimes the chuck will benefit from pulling it apart and cleaning it up.
Rebuilding a DP is probably a weekend project for someone with some tools and mechanical ability. It's a bit ridiculous, but i've got 5 drill presses in my shop right now - a Walker Turner floor model from the late 1930's, a 1980's Taiwanese model heavily tweaked by my machinist father, a mid 1930's Delta floor "220" model, a 15" Atlas bench top model, and a small benchtop Craftsman (1940's i think). The Walker Turner i bought at an estate sale for $80. After a new belt and electrical cord, it's my daily user. The Taiwanese model is also a daily user set up for metal work - i traded my Dad for a 1950's South Bend floor model that i paid $12 for (but didn't really want another floor model). The Delta and Atlas are awaiting rebuilds this winter and will get sent off to their new homes (one for my nephew, the other for a friend). The small Craftsman is my 10 year old son's. I've also had a 15" Buffalo camelback floor model from the 1890's. It's an absolute beast and is currently in my Dad's shop. He uses it for the heavy duty work. I also passed a 14" Duro bench top model on to one of my brothers. It's also a nice machine.
In my experience, the Atlas, Craftsman, Duro, and South Bend have been the easiest to rebuild. Bearings are common sizes, readily available, and inexpensive. The Atlas bearings cost me less than $30. Add a new belt, wiring, and paint and i had less than $70 into the rebuild of a very high quality and robust machine. It was a fun project too.
The Walker Turner is still on its original bearings. When those go, because of their rarity, it'll probably be $60 or more just for them. Bearings for the Delta 220 ran that much as well.
I enjoy rebuilding the old stuff. Even if you don't, Craigslist is a good source for newer used drill presses. If you know basically what you're looking for, it's probably hard to go wrong. I wouldn't get too hung up on brand. Most Taiwanese and Chinese DP's are very similar - look like they came out of the same factory. At that point, it's making sure they have whatever features you want (crank lift for the table, work light, etc.) and that they're complete and undamaged. If you can measure for runout when you're looking at a used tool, that's helpful too.
I'm also not too keen on laser guides or having a bazillion speeds. The guides are fine, but i don't rely on them for exacting work. Also, i've never been limited with the 4 speeds on my Walker Turner. My Taiwanese DP has 16 speeds - i think i've only ever used 3 of them. Work lights and table lifts are good to have, but i would never consider their absence a deal killer.
www.owwm.org and
www.vintagemachinery.org are good sources of information on the older equipment and how to work on it. Finding parts too.
paulh