I cut my teeth on manual machines without DRO's. I will use the DRO on occasion (especially when I have metric dimensions to work with), but the dials work well enough. You just need to make sure of your backlash when positioning.
In general, the bigger the casting means a more rigid machine. A more rigid machine makes holding dimensions much easier.
As mentioned above, the cost of the machine is only the first part. But, it is the thing that does not wear out very quickly, and can last a couple of lifetimes if taken care of. Nor do the hold downs, vices, indexers, rotary tables and the like wear out quickly. What does wear out are the cutters. Carbide cutters do wear longer, but will break if you look at them cross eyed. Plus they are much more expensive than highspeed steel cutters. And, you need a good assortment of cutters.
Two things that you need right away are a drill chuck and a milling vise. You will find that the mill will replace just about any drill press.
Calipers, micrometers, combination set (12 inch scale, 90/45 degree, head, centering head, and protracting head), parallels, 1-2-3 blocks. and v-blocks are things that you will need to start as well.
Note: Though I really like milling stuff, lathes are much more useful for most things. One can get quite creative and actually mill stuff on a lathe even without a milling attachment. Turning stuff on a mill is generally much more awkward; it can be done, however.