Round column is much less convenient than square column. With a square column benchtop mill or a knee mill with dovetailed slideways, you can change height when changing tasks or cutter, without losing your index. Typically having a knee to change elevation with is more precise and more rigid than only having the quill like on a mill/drill.
Bridgeports are nice, so are Tree mills, Lagun mills, Cinci Toolmasters, or Index/Wells-Index mills. They are all similar to Bridgeport more or less, in that they are vertical knee design, and with heads that nod and pivot, as well as a quill that can power feed, crank, or be used manually as a drill press. Power feed is nice to have, as is DRO.
I have an Index 645 knee mill from the 60's. A big solid beast that will take heavy cuts, and has x power feed. No digital readout, which would be nice.
It has a B&S #9 taper spindle, which is archaic but I have collets for it, which will do 95% of what I'll ever need. R-8 is more common, and grips well too. It seems picky to me to get hung up on R-8 for theoretically gripping less tightly than some other methods- they work quite well in my experience, and hold cutters up to the capacity of the machine.
If you buy a used mill, look for backlash in the feedscrews. A typical range is 10-30 thousandths for a nice tight screw, and up to .100" for a worn one. If it's a lot, that tells you the mill has seen hard use, or may have lubrication issues. Often the screw will be more worn in the center of table travel, then as cranked toward either end, will tighten up. That's because most of a mill's daily operations tend to occur near the center of the table.
Some mills have a split bronze nut for the feedscrews that can be adjusted to take up some backlash as it wears. Some will need to be replaced.
If you have a digital readout, it is easier to deal with having a pretty worn leadscrew- the DRO still tells you where you are or how far it is to a certain feature when you want to get back to it. How worn of a mill you'll buy depends on how optimistic/eager you are, or how much you are willing to work around idiosyncrasies in a machine.
I've had a JET-16 round column mill in the past, which was like a frustrating toy compared to my Index or any Bridgeport I've worked on. But, I love big old cast iron machines.