Hello Rick,
I agree with wawoodman: Stop even thinking of yourself as a hobbyist. You have a professional grade tool. I was a research scientist, and whenever I got a student, I would tell them that from the day they walked into my lab to think of themselves as professionals, even though they had only the vaguest idea what that meant. It made them OWN their work and also took things to a different level in terms of intensity, commitment, and the onus to really LEARN stuff. When I was a wee young lad and made my first appearance in the university machine shop, the head machinist there had an almost identical conversation with me. I took him seriously, and the machinists I worked with for 45 years after that always were very kind to me and taught me things for my entire career, probably because they could tell that I really WANTED to learn, and was willing to pay the price for the education. So no more "hobbyist" crap, ok? You are now a professional in training, just like the rest of us.
Now with respect to the Bridgeport:
I would recommend putting the Bijur system at the top of the list. A well lubed mill is a happy mill. I always recommend H&W (
H&W Machine Repair & Rebuilding - Parts and Service for the Metalworking Industry) for all things Bridgeport. Great folks, always helpful.
Get a manual for the mill. Ozark Woodworking amongst other places sells them. A service manual and parts diagram/list can also be very useful. Call H&W with the serial number and the model and they probably can point you to the right info.
Second I would put the Z axis feed. Get a real one, such as a servo. I am too clapped out to grind that heavy knee up and down all the time, but youngsters seem to enjoy the exercise. Personally, the drill type would not work for me, but many people like them. My opinion is that a Y axis power feed is pretty useless on a Bridgeport.
I would put a DRO at near the top of the list. maybe ahead of the Z axis power feed. I have a Newall DP1200 DRO on my mill, and another Newall on the lathe. Both installed by me. I HIGHLY recommend the Newall, as it is easy to install, VERY robust, accurate, very visible, good interface, and if you spend the extra for a high end one like the DP1200, there are many valuable functions. In any case, assuming you have an older mill, the backlash will make doing precision work a pain in the ass, although it CAN be done. My mill is overdue for a new X axis split nut, and has horrible backlash, but with the DRO and attention, I can usually hold around +/-0.001" if I want to. Even on simple jobs, where precision is "not necessary" the DRO will be an enormous help. The DRO is NOT the place to save a few bucks. It will, in all likelihood, be on the mill many, many years from now, and the leverage that a good one gives you over that time is HUGELY more valuable than the few bucks you might save on a cheap one. You will grow into it if it is a good one, rather than quickly outgrow it if it is very basic. Plus a good one makes using the tool a real pleasure. Opinions differ of course, as to which is best. Do you feel lucky, punk? well, DO you?
Next, get a bunch of R8 collets. If you look on EBAY you can get good used QUALITY collets such as Hardinge. New import collets are cheap, but in my experience, often are just crap. Then make a board to store them with dedicated tools you will use all the time, such as an edgefinder (get a Starrett, not an import), a selection of end mills (I use roughers a lot, so some of them live in dedicated collets), Drill chuck (best if with an integral R8), Boring head, and so on.
Soon, if you do a lot of work, and are decrepit like I am, your shoulders will insist that you get a power drawbar. I have a Maxi TorqueRite, and it is a lifesaver.
Get several good stops to allow easy removal and replacement of parts in the vise. The one on the Kurt is good, but not enough for all applications. There are lots of different varieties. Check Google images to get some ideas.
You will want some replacement jaws for the Kurt. I have a variety, but the ones with ground precision V grooves for holding round stock vertically or horizontally are really useful. Again, EBAY. There is a vendor that makes them that sells on EBAY.
You WILL need parallels, both thin and thick (1/4", 1/8"). Also a clamping kit for working off the table, A good dial indicator on a swing arm for tramming the mill, a fine precision DTI (0.0005" resolution) for indicating in parts, An Indicol or similar tool for holding the precision DTI into the spindle for indicating diameters, etc.
Eventually, you will want some precision V blocks, angle plate set, perhaps a sine bar.
A really useful thing to have is a variety of flat tooling plates which you can mount in your chuck. These are flat and square (thick aluminum) with a grid of tapped holes (1/2"-13 and 1/4"-20) that you can use with clamp screws and hold downs to hold odd parts. You can build this yourself. Be sure to tram the mill VERY well before you flycut or otherwise mill the surface. As the saying goes "the evil that men do lives after them, the good is often interred with their bones". hahaha. Ask me how I know about THIS one...
Finally, EBAY really IS your friend. You can get amazingly good deals on tools, tooling, and so on. Things like a spacer or rotary table, chucks, blocks, angle plates, and so on are often found at very affordable prices. There is a lot of used, but very usable old precision iron for manual machining out there, often at great prices.
Anyway, good luck with it. Be careful, don't climb mill steel (!!!), wear glasses, and don't forget to boogie!
All the best,
Michael